DD150613A5 - Verfahren zur herstellung von enaminen - Google Patents

Verfahren zur herstellung von enaminen Download PDF

Info

Publication number: DD150613A5
Authority: DD; German Democratic Republic
Prior art keywords: oxo; thia; hept; diazabicyclo; prop
Prior art date: 1979-05-08

Application number

DD80220942A

Other languages

German (de)

English (en)

Inventor

John R Corfield

Derek Johnson

Clifford G Taylor

Original Assignee

Lilly Industries Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-05-08

Filing date

1980-05-07

Publication date

1981-09-09

1980-05-07 Application filed by Lilly Industries Ltd filed Critical Lilly Industries Ltd

1981-09-09 Publication of DD150613A5 publication Critical patent/DD150613A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 13
150000002081 enamines Chemical class 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 31
238000006243 chemical reaction Methods 0.000 claims abstract description 23
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 17
150000002085 enols Chemical class 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
239000011574 phosphorus Substances 0.000 claims abstract description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 8
150000001412 amines Chemical class 0.000 claims abstract description 8
125000002252 acyl group Chemical group 0.000 claims abstract description 7
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
125000005842 heteroatom Chemical group 0.000 claims abstract description 3
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
-1 X Chemical compound 0.000 claims description 220
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 8
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
150000001540 azides Chemical class 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
150000002825 nitriles Chemical class 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 2
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims 2
125000002843 carboxylic acid group Chemical group 0.000 claims 1
239000003242 anti bacterial agent Substances 0.000 abstract description 6
150000001732 carboxylic acid derivatives Chemical group 0.000 abstract description 6
239000000543 intermediate Substances 0.000 abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 abstract description 4
101100354192 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) exp5 gene Proteins 0.000 abstract 3
101100505001 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) glpO gene Proteins 0.000 abstract 2
102100032837 Exportin-6 Human genes 0.000 abstract 1
101710147891 Exportin-6 Proteins 0.000 abstract 1
101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 1
101150109310 msrAB1 gene Proteins 0.000 abstract 1
239000000376 reactant Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
239000000243 solution Substances 0.000 description 46
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
229910019142 PO4 Inorganic materials 0.000 description 40
239000010452 phosphate Substances 0.000 description 40
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 34
239000011541 reaction mixture Substances 0.000 description 34
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
238000003756 stirring Methods 0.000 description 25
239000000203 mixture Substances 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 23
229910052943 magnesium sulfate Inorganic materials 0.000 description 22
235000019341 magnesium sulphate Nutrition 0.000 description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
239000006260 foam Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
239000012299 nitrogen atmosphere Substances 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000377 silicon dioxide Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
229940124587 cephalosporin Drugs 0.000 description 8
ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
229930186147 Cephalosporin Natural products 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
125000004442 acylamino group Chemical group 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
239000002253 acid Substances 0.000 description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
150000001780 cephalosporins Chemical class 0.000 description 5
239000000284 extract Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000002140 halogenating effect Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000007858 starting material Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical group OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
QEJXQVSIYPMBQC-UHFFFAOYSA-N [chloro(phenyl)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1P(=O)(Cl)OC1=CC=CC=C1 QEJXQVSIYPMBQC-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
WVPKAWVFTPWPDB-UHFFFAOYSA-M dichlorophosphinate Chemical compound [O-]P(Cl)(Cl)=O WVPKAWVFTPWPDB-UHFFFAOYSA-M 0.000 description 3
238000001914 filtration Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
YCGHMIAXHZJKML-UHFFFAOYSA-N prop-1-en-2-yl dihydrogen phosphate Chemical compound CC(=C)OP(O)(O)=O YCGHMIAXHZJKML-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
MSJBRVIZZHKNPL-BDPMCISCSA-N (4-nitrophenyl)methyl (6r)-3-hydroxy-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)O)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)COC1=CC=CC=C1 MSJBRVIZZHKNPL-BDPMCISCSA-N 0.000 description 2
ZUBXPSDFPQTKQN-ZCFIWIBFSA-N (6r)-3-hydroxy-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC(O)=CN2C(=O)C[C@H]21 ZUBXPSDFPQTKQN-ZCFIWIBFSA-N 0.000 description 2
WICSNEYXWVFTCL-UHFFFAOYSA-N 1-[chloro-(4-methoxyphenyl)phosphoryl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1P(Cl)(=O)C1=CC=C(OC)C=C1 WICSNEYXWVFTCL-UHFFFAOYSA-N 0.000 description 2
OKJRGVBPULHBAI-UHFFFAOYSA-N 1-[chloro-(4-nitrophenyl)phosphoryl]-4-nitrobenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1P(Cl)(=O)C1=CC=C([N+]([O-])=O)C=C1 OKJRGVBPULHBAI-UHFFFAOYSA-N 0.000 description 2
ZMSZULXBULRXPM-UHFFFAOYSA-N 1-chloro-2-[chloro-(2-chlorophenyl)phosphoryl]benzene Chemical compound ClC1=CC=CC=C1P(Cl)(=O)C1=CC=CC=C1Cl ZMSZULXBULRXPM-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HKYSIUYOULVHTO-UHFFFAOYSA-N [chloro(cyclohexyl)phosphoryl]cyclohexane Chemical compound C1CCCCC1P(=O)(Cl)C1CCCCC1 HKYSIUYOULVHTO-UHFFFAOYSA-N 0.000 description 2
125000005360 alkyl sulfoxide group Chemical group 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
239000012267 brine Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
150000001733 carboxylic acid esters Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 2
KTLIMPGQZDZPSB-UHFFFAOYSA-M diethylphosphinate Chemical compound CCP([O-])(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-M 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000007306 functionalization reaction Methods 0.000 description 2
125000004970 halomethyl group Chemical group 0.000 description 2
OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000012453 solvate Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VWEAZVFNLFJJSV-UHFFFAOYSA-N (4-methoxyphenyl)phosphinic acid Chemical compound COC1=CC=C(P(O)=O)C=C1 VWEAZVFNLFJJSV-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
JVQNKZPGPIESSJ-UHFFFAOYSA-N 1-[bromo(ethyl)phosphoryl]ethane Chemical compound CCP(Br)(=O)CC JVQNKZPGPIESSJ-UHFFFAOYSA-N 0.000 description 1
DWKYPUBNMRTDEC-UHFFFAOYSA-N 1-[chloro(ethoxy)phosphoryl]-4-methoxybenzene Chemical compound CCOP(Cl)(=O)C1=CC=C(OC)C=C1 DWKYPUBNMRTDEC-UHFFFAOYSA-N 0.000 description 1
BZVLBOJZJVECBW-UHFFFAOYSA-N 1-[chloro(ethoxy)phosphoryl]-4-methylbenzene Chemical compound CCOP(Cl)(=O)C1=CC=C(C)C=C1 BZVLBOJZJVECBW-UHFFFAOYSA-N 0.000 description 1
DOXZVLXVWQFTJU-UHFFFAOYSA-N 1-[chloro(ethoxy)phosphoryl]-4-nitrobenzene Chemical compound CCOP(Cl)(=O)C1=CC=C([N+]([O-])=O)C=C1 DOXZVLXVWQFTJU-UHFFFAOYSA-N 0.000 description 1
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YBHVCGKQTSXMAF-UHFFFAOYSA-N 1-butoxy-3-[(3-butoxyphenyl)-chlorophosphoryl]benzene Chemical compound CCCCOC1=CC=CC(P(Cl)(=O)C=2C=C(OCCCC)C=CC=2)=C1 YBHVCGKQTSXMAF-UHFFFAOYSA-N 0.000 description 1
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MXTJPOSNUKYRFM-UHFFFAOYSA-N 1-chloro-3-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC(OP(Cl)(Cl)=O)=C1 MXTJPOSNUKYRFM-UHFFFAOYSA-N 0.000 description 1
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RNXHHJQBVBRJMB-UHFFFAOYSA-N 1-dichlorophosphoryloxybutane Chemical compound CCCCOP(Cl)(Cl)=O RNXHHJQBVBRJMB-UHFFFAOYSA-N 0.000 description 1
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CPNIHFWTOIRLCG-UHFFFAOYSA-N 2-chloro-4-dichlorophosphoryloxy-1-methylbenzene Chemical compound CC1=CC=C(OP(Cl)(Cl)=O)C=C1Cl CPNIHFWTOIRLCG-UHFFFAOYSA-N 0.000 description 1
XAWJSDHWXDVXDH-UHFFFAOYSA-N 2-dichlorophosphoryloxypropane Chemical compound CC(C)OP(Cl)(Cl)=O XAWJSDHWXDVXDH-UHFFFAOYSA-N 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
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125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
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AWMNSIIUIIBIQG-UHFFFAOYSA-N 4-[bromo-(3,4-dichlorophenyl)phosphoryl]-1,2-dichlorobenzene Chemical compound C1=C(Cl)C(Cl)=CC=C1P(Br)(=O)C1=CC=C(Cl)C(Cl)=C1 AWMNSIIUIIBIQG-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
229910014265 BrCl Inorganic materials 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
BFPNHDHAGYLBRT-UHFFFAOYSA-N C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)C#N.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-] Chemical compound C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)C#N.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-] BFPNHDHAGYLBRT-UHFFFAOYSA-N 0.000 description 1
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QRBTYGBPHJQLLK-UHFFFAOYSA-N C1=CC=C(C=C1)CC2=NC3C(S2)N(C3=O)C(=C(C(C4=CC=CC=C4)C5=CC=CC=C5)OP(=O)(O)O)C(=O)OC(C6=CC=CC=C6)C7=CC=CC=C7 Chemical compound C1=CC=C(C=C1)CC2=NC3C(S2)N(C3=O)C(=C(C(C4=CC=CC=C4)C5=CC=CC=C5)OP(=O)(O)O)C(=O)OC(C6=CC=CC=C6)C7=CC=CC=C7 QRBTYGBPHJQLLK-UHFFFAOYSA-N 0.000 description 1
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XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
241000065675 Cyclops Species 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
OMOPIAOKQJWPEF-UHFFFAOYSA-N [bromo(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(Br)C1=CC=CC=C1 OMOPIAOKQJWPEF-UHFFFAOYSA-N 0.000 description 1
LJQYRVTVCLYUTJ-UHFFFAOYSA-N [bromo(phenyl)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1P(=O)(Br)OC1=CC=CC=C1 LJQYRVTVCLYUTJ-UHFFFAOYSA-N 0.000 description 1
XQMXIXSAOJZXIZ-UHFFFAOYSA-N [chloro(cyclohexyl)phosphoryl]oxybenzene Chemical compound C1CCCCC1P(=O)(Cl)OC1=CC=CC=C1 XQMXIXSAOJZXIZ-UHFFFAOYSA-N 0.000 description 1
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MGQNGBFGJVYIEG-UHFFFAOYSA-N [chloro(cyclooctyl)phosphoryl]cyclooctane Chemical compound C1CCCCCCC1P(=O)(Cl)C1CCCCCCC1 MGQNGBFGJVYIEG-UHFFFAOYSA-N 0.000 description 1
DYLBZNYNXHTQBA-UHFFFAOYSA-N [chloro(cyclopentyl)phosphoryl]cyclopentane Chemical compound C1CCCC1P(=O)(Cl)C1CCCC1 DYLBZNYNXHTQBA-UHFFFAOYSA-N 0.000 description 1
LWMUQLPKUXIHDY-UHFFFAOYSA-N [chloro(cyclopentyloxy)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(Cl)OC1CCCC1 LWMUQLPKUXIHDY-UHFFFAOYSA-N 0.000 description 1
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239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
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RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
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150000007942 carboxylates Chemical class 0.000 description 1
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239000003610 charcoal Substances 0.000 description 1
JZPDBTOWHLZQFC-UHFFFAOYSA-N chloro-di(propan-2-yl)phosphane Chemical compound CC(C)P(Cl)C(C)C JZPDBTOWHLZQFC-UHFFFAOYSA-N 0.000 description 1
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238000004140 cleaning Methods 0.000 description 1
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239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
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VZUNXXUSMINMCM-UHFFFAOYSA-N dibromophosphoryloxymethane Chemical compound COP(Br)(Br)=O VZUNXXUSMINMCM-UHFFFAOYSA-N 0.000 description 1
125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
FCYHXMMAKHJFJB-UHFFFAOYSA-N dichlorophosphoryloxycyclopropane Chemical compound ClP(Cl)(=O)OC1CC1 FCYHXMMAKHJFJB-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
GOJNABIZVJCYFL-UHFFFAOYSA-M dimethylphosphinate Chemical compound CP(C)([O-])=O GOJNABIZVJCYFL-UHFFFAOYSA-M 0.000 description 1
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230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000005530 etching Methods 0.000 description 1
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239000012458 free base Substances 0.000 description 1
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229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
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FBKDEECWCACPLH-UHFFFAOYSA-N methyl 2-oxo-1,3-dihydroindole-4-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1CC(=O)N2 FBKDEECWCACPLH-UHFFFAOYSA-N 0.000 description 1
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235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
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ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
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239000012047 saturated solution Substances 0.000 description 1
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238000003786 synthesis reaction Methods 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD80220942A 1979-05-08 1980-05-07 Verfahren zur herstellung von enaminen DD150613A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7915929		1979-05-08

Publications (1)

Publication Number	Publication Date
DD150613A5 true DD150613A5 (de)	1981-09-09

Family

ID=10505015

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80220942A DD150613A5 (de)	1979-05-08	1980-05-07	Verfahren zur herstellung von enaminen

Country Status (33)

Country	Link
US (1)	US4301280A (pl)
EP (1)	EP0019401B1 (pl)
JP (1)	JPS55151589A (pl)
KR (1)	KR840000484B1 (pl)
AR (1)	AR226430A1 (pl)
AT (1)	AT369746B (pl)
AU (1)	AU540210B2 (pl)
BE (1)	BE883101A (pl)
BG (1)	BG36633A3 (pl)
CA (1)	CA1148938A (pl)
CH (1)	CH647526A5 (pl)
CS (1)	CS219919B2 (pl)
DD (1)	DD150613A5 (pl)
DE (1)	DE3067099D1 (pl)
DK (1)	DK171892B1 (pl)
EG (1)	EG14897A (pl)
ES (1)	ES491248A0 (pl)
FI (1)	FI75170C (pl)
FR (1)	FR2456112A1 (pl)
GR (1)	GR68417B (pl)
HU (1)	HU184753B (pl)
IE (1)	IE49786B1 (pl)
IL (1)	IL59991A (pl)
IT (1)	IT1188934B (pl)
LU (1)	LU82423A1 (pl)
NZ (1)	NZ193619A (pl)
PH (1)	PH15984A (pl)
PL (1)	PL121466B1 (pl)
PT (1)	PT71186B (pl)
RO (1)	RO81342B (pl)
SU (1)	SU1042619A3 (pl)
YU (1)	YU121180A (pl)
ZA (1)	ZA802718B (pl)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0133670A3 (de) *	1983-08-09	1985-12-18	Bayer Ag	Verfahren zur Herstellung von 7-Acylamino-3-hydrocy-cephem-4-carbonsäuren und 7-Acylamino-3-hydroxy-1-de-thia-1-oxacephem-4-carbonsäuren
US5604222A (en) *	1993-12-27	1997-02-18	Lupin Laboratories, Ltd.	Method for the preparation of 2-chloro sulfinyl azetidinones
US5578721A (en) *	1994-07-11	1996-11-26	Lupin Laboratories Limited	Process for preparation of 3-exomethylene cepham sulfoxide esters
CN111647638A (zh) *	2020-04-17	2020-09-11	江苏正泰药业有限公司	一种7-anca的制备工艺

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS51105051A (pl) *	1975-02-21	1976-09-17	Shionogi Seiyaku Kk
JPS609516B2 (ja) *	1975-03-07	1985-03-11	塩野義製薬株式会社	セフエム骨格の環化製法
CA1136132A (en) *	1975-02-17	1982-11-23	Teruji Tsuji	Cyclization to form cephem ring and intermediates therefor
JPS5214789A (en) *	1975-07-22	1977-02-03	Shionogi & Co Ltd	Process for preparing 3-substiuted cephem compounds by ring closure
JPS5858355B2 (ja) *	1976-01-01	1983-12-24	塩野義製薬株式会社	オキソチアゾリノアゼチジニルハロブテン酸類
US4226986A (en) *	1979-02-01	1980-10-07	Eli Lilly And Company	Process for halogenation of β-lactam compounds

1980
- 1980-04-09 CA CA000349470A patent/CA1148938A/en not_active Expired
- 1980-05-01 US US06/145,531 patent/US4301280A/en not_active Expired - Lifetime
- 1980-05-02 PH PH23978A patent/PH15984A/en unknown
- 1980-05-02 EP EP80301457A patent/EP0019401B1/en not_active Expired
- 1980-05-02 BE BE6/47157A patent/BE883101A/fr not_active IP Right Cessation
- 1980-05-02 AU AU58042/80A patent/AU540210B2/en not_active Expired
- 1980-05-02 GR GR61834A patent/GR68417B/el unknown
- 1980-05-02 DE DE8080301457T patent/DE3067099D1/de not_active Expired
- 1980-05-05 PT PT71186A patent/PT71186B/pt unknown
- 1980-05-05 LU LU82423A patent/LU82423A1/fr unknown
- 1980-05-05 AT AT0238980A patent/AT369746B/de not_active IP Right Cessation
- 1980-05-05 RO RO101039A patent/RO81342B/ro unknown
- 1980-05-05 DK DK196580A patent/DK171892B1/da not_active IP Right Cessation
- 1980-05-05 NZ NZ193619A patent/NZ193619A/xx unknown
- 1980-05-05 FR FR8009957A patent/FR2456112A1/fr active Granted
- 1980-05-05 IL IL59991A patent/IL59991A/xx unknown
- 1980-05-06 HU HU801102A patent/HU184753B/hu unknown
- 1980-05-06 CH CH3509/80A patent/CH647526A5/fr not_active IP Right Cessation
- 1980-05-06 IT IT48597/80A patent/IT1188934B/it active
- 1980-05-06 IE IE926/80A patent/IE49786B1/en not_active IP Right Cessation
- 1980-05-06 FI FI801452A patent/FI75170C/fi not_active IP Right Cessation
- 1980-05-06 JP JP5985980A patent/JPS55151589A/ja active Granted
- 1980-05-06 ZA ZA00802718A patent/ZA802718B/xx unknown
- 1980-05-07 BG BG047661A patent/BG36633A3/xx not_active Expired
- 1980-05-07 EG EG282/80A patent/EG14897A/xx active
- 1980-05-07 ES ES491248A patent/ES491248A0/es active Granted
- 1980-05-07 YU YU01211/80A patent/YU121180A/xx unknown
- 1980-05-07 DD DD80220942A patent/DD150613A5/de unknown
- 1980-05-07 AR AR280923A patent/AR226430A1/es active
- 1980-05-07 SU SU802920001A patent/SU1042619A3/ru active
- 1980-05-07 CS CS803210A patent/CS219919B2/cs unknown
- 1980-05-08 KR KR1019800001826A patent/KR840000484B1/ko active
- 1980-05-08 PL PL1980224114A patent/PL121466B1/pl unknown

Also Published As

Publication number	Publication date
FI75170B (fi)	1988-01-29
JPS55151589A (en)	1980-11-26
BG36633A3 (en)	1984-12-16
PL224114A1 (pl)	1981-02-13
ZA802718B (en)	1981-11-25
JPH0222078B2 (pl)	1990-05-17
FI801452A (fi)	1980-11-09
PT71186A (en)	1980-06-01
DK196580A (da)	1980-11-09
RO81342B (ro)	1983-04-30
FR2456112B1 (pl)	1984-03-23
CS219919B2 (en)	1983-03-25
BE883101A (fr)	1980-11-03
YU121180A (en)	1984-04-30
IE800926L (en)	1980-11-08
EP0019401B1 (en)	1984-03-21
GR68417B (pl)	1981-12-29
NZ193619A (en)	1982-03-30
IL59991A0 (en)	1980-07-31
KR840000484B1 (ko)	1984-04-12
IE49786B1 (en)	1985-12-11
IT1188934B (it)	1988-01-28
PL121466B1 (en)	1982-05-31
AU540210B2 (en)	1984-11-08
HU184753B (en)	1984-10-29
ATA238980A (de)	1982-06-15
CH647526A5 (fr)	1985-01-31
KR830002788A (ko)	1983-05-30
PT71186B (en)	1983-01-10
ES8104309A1 (es)	1981-04-16
SU1042619A3 (ru)	1983-09-15
DK171892B1 (da)	1997-08-04
CA1148938A (en)	1983-06-28
ES491248A0 (es)	1981-04-16
FR2456112A1 (fr)	1980-12-05
IT8048597A0 (it)	1980-05-06
AR226430A1 (es)	1982-07-15
AT369746B (de)	1983-01-25
DE3067099D1 (en)	1984-04-26
LU82423A1 (fr)	1982-01-20
EG14897A (en)	1985-06-30
PH15984A (en)	1983-05-18
AU5804280A (en)	1980-11-13
RO81342A (ro)	1983-04-29
US4301280A (en)	1981-11-17
IL59991A (en)	1983-03-31
EP0019401A1 (en)	1980-11-26
FI75170C (fi)	1988-05-09
IT8048597A1 (it)	1981-11-06

Publication	Publication Date	Title
DE69331089T2 (de)	2002-07-18	Beta-Laktam und Cepham Verbindungen und Ihre Herstellung
DE2606278C2 (pl)	1989-05-03
DD154542A5 (de)	1982-03-31	Verfahren zur herstellung von 6 beta-hydroxyalkylpenicillansaeuren
DE3429102A1 (de)	1985-02-28	Verfahren zur herstellung von penem-verbindungen
CH617677A5 (pl)	1980-06-13
DE2735454A1 (de)	1978-02-23	Verfahren zur herstellung von 3-chlorcephemverbindungen
DD150613A5 (de)	1981-09-09	Verfahren zur herstellung von enaminen
DE2254631A1 (de)	1973-10-04	Substituierte ceph-3-eme
DE2912483A1 (de)	1979-10-11	Beta -lactamverbindungen, verfahren zu deren herstellung und arzneimittel
DE2303889A1 (de)	1973-08-02	Antibiotika
DE2952413A1 (de)	1980-07-17	3-halogencarbacephem-verbindungen
CH627161A5 (pl)	1981-12-31
DE2651771A1 (de)	1977-05-26	7-amino-3-methyl-1-oxadethia-3- cephem-4-carbonsaeure-derivate, verfahren zu ihrer herstellung, arzneimittel und zwischenprodukte
DE2107650A1 (pl)	1971-09-02
DE2254644A1 (de)	1973-07-19	Substituierte ceph-3-eme und ceph-3-em-sulfoxide und verfahren zu ihrer herstellung
DE2534926A1 (de)	1976-02-19	Sauerstoffanaloge von cephalosporinen
DE2215039A1 (de)	1972-10-26	Neue Acyloxyalkylesterderivate von Penicillin und Cephalosporin
DE2534337C2 (de)	1986-05-07	Verfahren zur Deacylierung von Benzylpenicillin oder einem Metall- oder Ammoniumsalz davon oder einem Cephalosporin C-Derivat
DE2702552C2 (de)	1986-08-21	7&alpha;-Methoxy-cephalosporine und Verfahren zur Herstellung derselben
CH620444A5 (en)	1980-11-28	Process for the preparation of bicyclic unsaturated thiaaza compounds
DE2440142A1 (de)	1975-03-13	Cephalosporinderivate und verfahren zu ihrer herstellung
CH626604A5 (en)	1981-11-30	Process for the preparation of sulphinylazetidinone compounds
DD153374A5 (de)	1982-01-06	Verfahren zur herstellung von beta-lactamen
DE2716814C2 (pl)	1987-11-26
DE2065489A1 (de)	1973-10-18	Cephalosporin c-derivate