BE426752A - - Google Patents

Info

Publication number

BE426752A

BE426752A BE426752DA BE426752A BE 426752 A BE426752 A BE 426752A BE 426752D A BE426752D A BE 426752DA BE 426752 A BE426752 A BE 426752A

Authority

BE

Belgium

Prior art keywords

acid

solution

hydroxyl group

desc

page number

Prior art date

Links

• Espacenet
• Global Dossier
• Discuss

• 239000007858 starting material Substances 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 239000011541 reaction mixture Substances 0.000 claims description 5
• 239000007800 oxidant agent Substances 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 2
• 150000002576 ketones Chemical class 0.000 claims description 2
• 239000000463 material Substances 0.000 claims description 2
• 150000003839 salts Chemical class 0.000 claims 1
• 239000011780 sodium chloride Substances 0.000 claims 1
• KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 12
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
• 150000001875 compounds Chemical class 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 230000003647 oxidation Effects 0.000 description 9
• 238000007254 oxidation reaction Methods 0.000 description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
• 238000000034 method Methods 0.000 description 7
• 239000002253 acid Substances 0.000 description 6
• 239000000203 mixture Substances 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 238000006731 degradation reaction Methods 0.000 description 5
• 239000000047 product Substances 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• 238000007792 addition Methods 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• 230000015556 catabolic process Effects 0.000 description 3
• 230000004059 degradation Effects 0.000 description 3
• 229910052736 halogen Inorganic materials 0.000 description 3
• 150000002367 halogens Chemical class 0.000 description 3
• 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 238000010525 oxidative degradation reaction Methods 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
• ORNBQBCIOKFOEO-QGVNFLHTSA-N Pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 description 2
• 229960000249 Pregnenolone Drugs 0.000 description 2
• ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• -1 benzal Chemical class 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 239000007795 chemical reaction product Substances 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 230000001264 neutralization Effects 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 235000011121 sodium hydroxide Nutrition 0.000 description 2
• 239000000052 vinegar Substances 0.000 description 2
• HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
• FMSSVYNONQQPON-CDQKXPLWSA-N (8R,9S,10S,13R,14S,17R)-3-methoxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C1C[C@@H]2[C@@]3(C)CCC(OC)CC3CC[C@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@]21C FMSSVYNONQQPON-CDQKXPLWSA-N 0.000 description 1
• 101700081261 AVEN Proteins 0.000 description 1
• FMGSKLZLMKYGDP-USOAJAOKSA-N Dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 1
• DNVPQKQSNYMLRS-APGDWVJJSA-N Ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-APGDWVJJSA-N 0.000 description 1
• 229940088597 Hormone Drugs 0.000 description 1
• RJKFOVLPORLFTN-STHVQZNPSA-N Progesterone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC(=O)CC4)CC3)CC2)CC1 RJKFOVLPORLFTN-STHVQZNPSA-N 0.000 description 1
• DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
• 229940083599 Sodium Iodide Drugs 0.000 description 1
• RJKFOVLPORLFTN-LEKSSAKUSA-N Syngestrets Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 125000004432 carbon atoms Chemical group C* 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 150000001845 chromium compounds Chemical class 0.000 description 1
• 230000001684 chronic Effects 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 238000010494 dissociation reaction Methods 0.000 description 1
• 230000005593 dissociations Effects 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 238000005658 halogenation reaction Methods 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000006011 modification reaction Methods 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 229960002847 prasterone Drugs 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 239000000186 progesterone Substances 0.000 description 1
• 229960003387 progesterone Drugs 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 150000007659 semicarbazones Chemical class 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• HLFCZZKCHVSOAP-DAMYXMBDSA-M sodium;(5Z)-5-(carbamoylhydrazinylidene)-1-methyl-6-oxo-2,3-dihydroindole-2-sulfonate Chemical compound [Na+].NC(=O)N/N=C/1C(=O)C=C2N(C)C(S([O-])(=O)=O)CC2=C\1 HLFCZZKCHVSOAP-DAMYXMBDSA-M 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 238000001256 steam distillation Methods 0.000 description 1
• HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
• KZJWDPNRJALLNS-VJSFXXLFSA-N β-Sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1