JPH047739B2 - - Google Patents

Info

Publication number: JPH047739B2
Authority: JP; Japan
Prior art keywords: general formula; diethyl ether; mmol; represented; hydroxyethyl
Prior art date: 1984-11-05
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

JP59231152A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61109763A (ja

Inventor

Masakatsu Shibazaki

Takamasa Iimori

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sagami Chemical Research Institute

Original Assignee

Sagami Chemical Research Institute

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.)

1984-11-05

Filing date

1984-11-05

Publication date

1992-02-12

1984-11-05 Application filed by Sagami Chemical Research Institute filed Critical Sagami Chemical Research Institute

1984-11-05 Priority to JP59231152A priority Critical patent/JPS61109763A/ja

1985-11-01 Priority to EP85113926A priority patent/EP0181581B1/fr

1985-11-01 Priority to DE8585113926T priority patent/DE3563741D1/de

1985-11-04 Priority to US06/794,893 priority patent/US4728746A/en

1986-05-28 Publication of JPS61109763A publication Critical patent/JPS61109763A/ja

1992-02-12 Publication of JPH047739B2 publication Critical patent/JPH047739B2/ja

Status Granted legal-status Critical Current

Links

MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 16
150000002466 imines Chemical class 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 7
150000001639 boron compounds Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
229910052796 boron Inorganic materials 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 93
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
239000002904 solvent Substances 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000010898 silica gel chromatography Methods 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
238000000034 method Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
-1 monocyclic β-lactam Chemical class 0.000 description 9
238000003756 stirring Methods 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 5
239000003782 beta lactam antibiotic agent Substances 0.000 description 5
YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 5
239000002132 β-lactam antibiotic Substances 0.000 description 5
229940124586 β-lactam antibiotics Drugs 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
150000003952 β-lactams Chemical group 0.000 description 4
SVHGAHUUGQJELP-UHFFFAOYSA-N 3-[tert-butyl(dimethyl)silyl]oxybutanoic acid Chemical compound OC(=O)CC(C)O[Si](C)(C)C(C)(C)C SVHGAHUUGQJELP-UHFFFAOYSA-N 0.000 description 3
NXHUKDCGEGEZCX-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonan-9-yl trifluoromethanesulfonate Chemical compound C1CCC2CCCC1B2OS(=O)(=O)C(F)(F)F NXHUKDCGEGEZCX-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 3
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 3
125000003460 beta-lactamyl group Chemical group 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
HNIPKGUBNKJRLE-UHFFFAOYSA-N phenylsulfanyl 3-hydroxybutanoate Chemical compound CC(O)CC(=O)OSC1=CC=CC=C1 HNIPKGUBNKJRLE-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
KOXGGQRWBCBIBI-UHFFFAOYSA-N 1-benzyl-3-(1-hydroxyethyl)-4-(2-phenylmethoxyethyl)azetidin-2-one Chemical compound C=1C=CC=CC=1CN1C(=O)C(C(O)C)C1CCOCC1=CC=CC=C1 KOXGGQRWBCBIBI-UHFFFAOYSA-N 0.000 description 2
ANSYAMHYCYOWAW-UHFFFAOYSA-N 3-phenylmethoxypropanal Chemical compound O=CCCOCC1=CC=CC=C1 ANSYAMHYCYOWAW-UHFFFAOYSA-N 0.000 description 2
YKIORMQJUHPDNW-UHFFFAOYSA-N 7-(1-hydroxyethyl)-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octan-8-one Chemical compound C1COC(C)(C)N2C(=O)C(C(O)C)C21 YKIORMQJUHPDNW-UHFFFAOYSA-N 0.000 description 2
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000009776 industrial production Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
YMQKYTUCHSHLJI-UHFFFAOYSA-N methyl 3-[tert-butyl(dimethyl)silyl]oxybutanoate Chemical compound COC(=O)CC(C)O[Si](C)(C)C(C)(C)C YMQKYTUCHSHLJI-UHFFFAOYSA-N 0.000 description 2
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
VSFDFXVTODBZBR-UHFFFAOYSA-N phenylsulfanyl 3-[tert-butyl(dimethyl)silyl]oxybutanoate Chemical compound CC(C)(C)[Si](C)(C)OC(C)CC(=O)OSC1=CC=CC=C1 VSFDFXVTODBZBR-UHFFFAOYSA-N 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000005185 salting out Methods 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
KKODTABNKDRKAY-UHFFFAOYSA-N 2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octan-8-one Chemical compound CC1(C)OCCC2CC(=O)N12 KKODTABNKDRKAY-UHFFFAOYSA-N 0.000 description 1
KMZSRAYQEJTJGC-UHFFFAOYSA-N 2-(1-hydroxyethyl)pentanoic acid Chemical compound CCCC(C(C)O)C(O)=O KMZSRAYQEJTJGC-UHFFFAOYSA-N 0.000 description 1
NPHULPIAPWNOOH-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(2,3-dihydroindol-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCC2=CC=CC=C12 NPHULPIAPWNOOH-UHFFFAOYSA-N 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
GNXPCTNTBWFGIV-UHFFFAOYSA-N 7-[1-[tert-butyl(dimethyl)silyl]oxyethyl]-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octan-8-one Chemical compound C1COC(C)(C)N2C(=O)C(C(O[Si](C)(C)C(C)(C)C)C)C21 GNXPCTNTBWFGIV-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
108090000204 Dipeptidase 1 Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
LDLDJEAVRNAEBW-UHFFFAOYSA-N Methyl 3-hydroxybutyrate Chemical compound COC(=O)CC(C)O LDLDJEAVRNAEBW-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
NZVFQVWFJMHEJN-ULUSZKPHSA-N S-butan-2-yl (3R)-3-hydroxybutanethioate Chemical compound CCC(C)SC(=O)C[C@@H](C)O NZVFQVWFJMHEJN-ULUSZKPHSA-N 0.000 description 1
MIHSVRIECQOFCF-ZCFIWIBFSA-N S-propan-2-yl (3R)-3-hydroxybutanethioate Chemical compound CC(C)SC(=O)C[C@@H](C)O MIHSVRIECQOFCF-ZCFIWIBFSA-N 0.000 description 1
PDQYWEQJGDPFHD-ZCFIWIBFSA-N S-propyl (3R)-3-hydroxybutanethioate Chemical compound CCCSC(=O)C[C@@H](C)O PDQYWEQJGDPFHD-ZCFIWIBFSA-N 0.000 description 1
UTPBRCQFKVGPPW-ZCFIWIBFSA-N S-tert-butyl (3R)-3-hydroxybutanethioate Chemical compound C[C@@H](O)CC(=O)SC(C)(C)C UTPBRCQFKVGPPW-ZCFIWIBFSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
WLLIXJBWWFGEHT-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] trifluoromethanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F WLLIXJBWWFGEHT-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
102000006635 beta-lactamase Human genes 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
FAVAVMFXAKZTMV-UHFFFAOYSA-N dibutylboranyl trifluoromethanesulfonate Chemical compound CCCCB(CCCC)OS(=O)(=O)C(F)(F)F FAVAVMFXAKZTMV-UHFFFAOYSA-N 0.000 description 1
NSZIXDAISDDUFN-UHFFFAOYSA-N dicyclopentylboranyl trifluoromethanesulfonate Chemical compound C1CCCC1B(OS(=O)(=O)C(F)(F)F)C1CCCC1 NSZIXDAISDDUFN-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
VJHSOSLBABUFPS-UHFFFAOYSA-N n-benzyl-3-(oxan-3-yloxy)propan-1-imine Chemical compound C1CCOCC1OCCC=NCC1=CC=CC=C1 VJHSOSLBABUFPS-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
WVMCKZVPXJTFOE-UHFFFAOYSA-N phenylsulfanyl 3-(benzylamino)-2-(1-hydroxyethyl)-5-phenylmethoxypentanoate Chemical compound C=1C=CC=CC=1SOC(=O)C(C(O)C)C(NCC=1C=CC=CC=1)CCOCC1=CC=CC=C1 WVMCKZVPXJTFOE-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
KMUGAUMHBACBQU-RXMQYKEDSA-N s-ethyl (3r)-3-hydroxybutanethioate Chemical compound CCSC(=O)C[C@@H](C)O KMUGAUMHBACBQU-RXMQYKEDSA-N 0.000 description 1
PEUCMDBRULVFDB-MRVPVSSYSA-N s-phenyl (3r)-3-hydroxybutanethioate Chemical compound C[C@@H](O)CC(=O)SC1=CC=CC=C1 PEUCMDBRULVFDB-MRVPVSSYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
229960002898 threonine Drugs 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP59231152A 1984-11-05 1984-11-05 β−アミノチオ−ルエステル及びその製造方法 Granted JPS61109763A (ja)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
JP59231152A JPS61109763A (ja)	1984-11-05	1984-11-05	β−アミノチオ−ルエステル及びその製造方法
EP85113926A EP0181581B1 (fr)	1984-11-05	1985-11-01	Beta-Aminothiol esters et procédé de leur préparation
DE8585113926T DE3563741D1 (en)	1984-11-05	1985-11-01	Beta-aminothiol ester and process for preparing thereof
US06/794,893 US4728746A (en)	1984-11-05	1985-11-04	β-aminothiol ester and process for preparing thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59231152A JPS61109763A (ja)	1984-11-05	1984-11-05	β−アミノチオ−ルエステル及びその製造方法

Publications (2)

Publication Number	Publication Date
JPS61109763A JPS61109763A (ja)	1986-05-28
JPH047739B2 true JPH047739B2 (fr)	1992-02-12

Family

ID=16919104

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59231152A Granted JPS61109763A (ja)	1984-11-05	1984-11-05	β−アミノチオ−ルエステル及びその製造方法

Country Status (1)

Country	Link
JP (1)	JPS61109763A (fr)

1984
- 1984-11-05 JP JP59231152A patent/JPS61109763A/ja active Granted

Also Published As

Publication number	Publication date
JPS61109763A (ja)	1986-05-28

Publication	Publication Date	Title
JPH0586023A (ja)	1993-04-06	ベータラクタム抗生物質中間体
JP2640986B2 (ja)	1997-08-13	（１′ｒ，３ｓ）―３―（１′―ヒドロキシエチル）―アゼチジン―２―オン又はその誘導体の製造法
US4443373A (en)	1984-04-17	Process for the production of antibiotic penems
JPS60120885A (ja)	1985-06-28	ペネム類の製造方法
CA1256443A (fr)	1989-06-27	Methode de preparation de derives de la 4-acetoxy- 3-hydroxyethylazetidin-2-one
HU209952B (en)	1994-12-28	New process for producing optically active oxazolidine and imidazolidine derivatives
CA1327045C (fr)	1994-02-15	Derive azetidinone et procede pour sa preparation
JPH047739B2 (fr)	1992-02-12
US4769451A (en)	1988-09-06	Synthesis of carbapenems using n-substituted azetidinones
JPH066570B2 (ja)	1994-01-26	４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造法
Sasaki et al.	1992	Synthetic Studies of Carbapenem and Penem Antibiotics. II. Synthesis of 3-Acetyl-2-azetidinones by (2+ 2) Cycloaddition of Diketene and Schiff Bases
EP0209886B1 (fr)	1990-03-21	Ester bêta-aminothiole N-substitué et procédé pour sa fabrication
JPH0358339B2 (fr)	1991-09-05
US4740595A (en)	1988-04-26	Preparation of azetidinones via N-protected oxirancecarboxamide intermediates
JP3388874B2 (ja)	2003-03-24	β−ラクタム化合物の製造方法
US4421686A (en)	1983-12-20	4-Norbornyl-sulfonyl azetidinone intermediates and process for preparing (S)-3-acylamino-4-substituted-2-azetidinones
US4728746A (en)	1988-03-01	β-aminothiol ester and process for preparing thereof
JPH0657683B2 (ja)	1994-08-03	光学活性アミノ酸誘導体
US4973687A (en)	1990-11-27	Synthesis of carbapenems using N-substituted azetidinones
JP2620533B2 (ja)	1997-06-18	新規なアミノ酸誘導体
US5089609A (en)	1992-02-18	4-benzoyl azetidinones
JPH0649679B2 (ja)	1994-06-29	アゼチジノン誘導体
US4827006A (en)	1989-05-02	Preparation of azetidinones via novel protected intermediates
JPH0665195A (ja)	1994-03-08	β−ラクタム誘導体の新規な製造法
US4963670A (en)	1990-10-16	Preparation of azetidinones via novel protected intermediates