BE440459A - - Google Patents

Info

Publication number

BE440459A

BE440459A BE440459DA BE440459A BE 440459 A BE440459 A BE 440459A BE 440459D A BE440459D A BE 440459DA BE 440459 A BE440459 A BE 440459A

Authority

BE

Belgium

Prior art keywords

halogenated hydrogen

starting material

hydrogen

agent

derivatives

Prior art date

Links

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• 150000002431 hydrogen Chemical class 0.000 claims description 10
• 238000000034 method Methods 0.000 claims description 10
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 239000007858 starting material Substances 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 7
• 239000002904 solvent Substances 0.000 claims description 6
• 238000009835 boiling Methods 0.000 claims description 5
• 238000001816 cooling Methods 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 238000010992 reflux Methods 0.000 claims description 3
• 239000002253 acid Substances 0.000 claims description 2
• 125000001931 aliphatic group Chemical group 0.000 claims description 2
• 239000007795 chemical reaction product Substances 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 150000007530 organic bases Chemical class 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 239000000047 product Substances 0.000 claims description 2
• UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-Hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 1
• 125000001246 bromo group Chemical group Br* 0.000 claims 1
• 230000001131 transforming Effects 0.000 claims 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 238000001704 evaporation Methods 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• 239000000203 mixture Substances 0.000 description 6
• MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• 150000003839 salts Chemical class 0.000 description 4
• 239000011780 sodium chloride Substances 0.000 description 4
• 229910052938 sodium sulfate Inorganic materials 0.000 description 4
• 235000011152 sodium sulphate Nutrition 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
• 239000000052 vinegar Substances 0.000 description 3
• QVHPTAJAHUONLV-DYKIIFRCSA-N (3S,8S,9S,10R,13R,14S)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CC=C21 QVHPTAJAHUONLV-DYKIIFRCSA-N 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• 235000010233 benzoic acid Nutrition 0.000 description 2
• 239000006227 byproduct Substances 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 150000001875 compounds Chemical class 0.000 description 2
• 238000010828 elution Methods 0.000 description 2
• GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
• LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
• 230000001264 neutralization Effects 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• 235000006408 oxalic acid Nutrition 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 230000001225 therapeutic Effects 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• 229960003563 Calcium Carbonate Drugs 0.000 description 1
• JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
• 241001676573 Minium Species 0.000 description 1
• WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
• 229960003604 Testosterone Drugs 0.000 description 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
• 238000000862 absorption spectrum Methods 0.000 description 1
• 238000007792 addition Methods 0.000 description 1
• 230000001476 alcoholic Effects 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 239000003098 androgen Substances 0.000 description 1
• 230000001548 androgenic Effects 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
• CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 230000000875 corresponding Effects 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 150000008131 glucosides Chemical class 0.000 description 1
• 150000002366 halogen compounds Chemical class 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 230000001766 physiological effect Effects 0.000 description 1
• NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
• 239000001187 sodium carbonate Substances 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 238000005507 spraying Methods 0.000 description 1
• -1 steroid ketones Chemical class 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 230000001629 suppression Effects 0.000 description 1
• 238000005979 thermal decomposition reaction Methods 0.000 description 1
• 238000005292 vacuum distillation Methods 0.000 description 1