BE529972A - - Google Patents

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Publication number

BE529972A

BE529972A BE529972DA BE529972A BE 529972 A BE529972 A BE 529972A BE 529972D A BE529972D A BE 529972DA BE 529972 A BE529972 A BE 529972A

Authority

BE

Belgium

Prior art keywords

chloroform

solution

water

mixture

acetate

Prior art date

Links

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• 150000003431 steroids Chemical class 0.000 claims description 16
• 239000000126 substance Substances 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 60
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 45
• 239000000243 solution Substances 0.000 claims 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 33
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 30
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 24
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 24
• 239000000203 mixture Substances 0.000 claims 24
• 150000001875 compounds Chemical class 0.000 claims 22
• 238000000034 method Methods 0.000 claims 22
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 19
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 18
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 17
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 16
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 15
• 239000003638 chemical reducing agent Substances 0.000 claims 15
• 239000005977 Ethylene Substances 0.000 claims 14
• 229910052794 bromium Inorganic materials 0.000 claims 13
• 238000004364 calculation method Methods 0.000 claims 13
• 239000011541 reaction mixture Substances 0.000 claims 12
• 238000006722 reduction reaction Methods 0.000 claims 12
• 239000002904 solvent Substances 0.000 claims 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 11
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 10
• 229910002092 carbon dioxide Inorganic materials 0.000 claims 9
• 125000000468 ketone group Chemical group 0.000 claims 9
• 235000017557 sodium bicarbonate Nutrition 0.000 claims 9
• 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 9
• 229960000583 acetic acid Drugs 0.000 claims 8
• 239000001569 carbon dioxide Substances 0.000 claims 8
• 238000002844 melting Methods 0.000 claims 8
• 230000008018 melting Effects 0.000 claims 8
• 239000012071 phase Substances 0.000 claims 8
• 238000001953 recrystallisation Methods 0.000 claims 8
• FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims 7
• 229910021554 Chromium(II) chloride Inorganic materials 0.000 claims 7
• MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims 7
• MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims 7
• XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 claims 7
• 229940109126 chromous chloride Drugs 0.000 claims 7
• 229960004544 cortisone Drugs 0.000 claims 7
• 229910052739 hydrogen Inorganic materials 0.000 claims 7
• 239000000047 product Substances 0.000 claims 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
• ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 0.000 claims 6
• 229960003290 cortisone acetate Drugs 0.000 claims 6
• 239000013078 crystal Substances 0.000 claims 6
• 238000000354 decomposition reaction Methods 0.000 claims 6
• 239000007858 starting material Substances 0.000 claims 6
• 238000003756 stirring Methods 0.000 claims 6
• -1 3-ketone steroids Chemical class 0.000 claims 5
• 238000000862 absorption spectrum Methods 0.000 claims 5
• 230000015572 biosynthetic process Effects 0.000 claims 5
• 238000002425 crystallisation Methods 0.000 claims 5
• 230000008025 crystallization Effects 0.000 claims 5
• 150000002576 ketones Chemical class 0.000 claims 5
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 5
• 239000007787 solid Substances 0.000 claims 5
• 239000012453 solvate Substances 0.000 claims 5
• 238000012360 testing method Methods 0.000 claims 5
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims 4
• 238000010521 absorption reaction Methods 0.000 claims 4
• 239000002253 acid Substances 0.000 claims 4
• DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims 4
• 238000006243 chemical reaction Methods 0.000 claims 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
• 238000010992 reflux Methods 0.000 claims 4
• DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 4
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
• 239000008346 aqueous phase Substances 0.000 claims 3
• 239000007864 aqueous solution Substances 0.000 claims 3
• 125000004432 carbon atom Chemical group C* 0.000 claims 3
• LRCIYVMVWAMTKX-UHFFFAOYSA-L chromium(ii) acetate Chemical compound [Cr+2].CC([O-])=O.CC([O-])=O LRCIYVMVWAMTKX-UHFFFAOYSA-L 0.000 claims 3
• 238000001816 cooling Methods 0.000 claims 3
• 238000001704 evaporation Methods 0.000 claims 3
• 230000008020 evaporation Effects 0.000 claims 3
• 239000000284 extract Substances 0.000 claims 3
• 239000001257 hydrogen Substances 0.000 claims 3
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 3
• 229910000041 hydrogen chloride Inorganic materials 0.000 claims 3
• 239000000543 intermediate Substances 0.000 claims 3
• 230000003287 optical effect Effects 0.000 claims 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
• 239000011343 solid material Substances 0.000 claims 3
• 238000003786 synthesis reaction Methods 0.000 claims 3
• TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims 2
• VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 claims 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone 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 claims 2
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 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 claims 2
• 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 2
• 229910001115 Zinc-copper couple Inorganic materials 0.000 claims 2
• 125000002252 acyl group Chemical group 0.000 claims 2
• 230000001476 alcoholic effect Effects 0.000 claims 2
• 125000000217 alkyl group Chemical group 0.000 claims 2
• 229950005228 bromoform Drugs 0.000 claims 2
• 239000003153 chemical reaction reagent Substances 0.000 claims 2
• TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 claims 2
• 239000012043 crude product Substances 0.000 claims 2
• 238000000921 elemental analysis Methods 0.000 claims 2
• 238000000605 extraction Methods 0.000 claims 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 2
• 238000002329 infrared spectrum Methods 0.000 claims 2
• 239000010410 layer Substances 0.000 claims 2
• 230000031700 light absorption Effects 0.000 claims 2
• 229910052943 magnesium sulfate Inorganic materials 0.000 claims 2
• 235000019341 magnesium sulphate Nutrition 0.000 claims 2
• 239000000155 melt Substances 0.000 claims 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
• 230000007935 neutral effect Effects 0.000 claims 2
• 239000012299 nitrogen atmosphere Substances 0.000 claims 2
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims 2
• 239000003495 polar organic solvent Substances 0.000 claims 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
• 229940107700 pyruvic acid Drugs 0.000 claims 2
• 229920006395 saturated elastomer Polymers 0.000 claims 2
• 238000001228 spectrum Methods 0.000 claims 2
• 239000001119 stannous chloride Substances 0.000 claims 2
• 235000011150 stannous chloride Nutrition 0.000 claims 2
• 239000000725 suspension Substances 0.000 claims 2
• 238000005406 washing Methods 0.000 claims 2
• OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims 1
• RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 claims 1
• NIOCRRWZBFJEPT-GGLGBZJVSA-N (8S,9S,10R,13R,14S,17R)-4-bromo-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound BrC1C2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(CCC1=O)C)C)[C@H](C)CCCC(C)C NIOCRRWZBFJEPT-GGLGBZJVSA-N 0.000 claims 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
• OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
• LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
• 229910021559 Chromium(II) bromide Inorganic materials 0.000 claims 1
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
• DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 claims 1
• QOLRLLFJMZLYQJ-LOBDNJQFSA-N Hecogenin Chemical compound O([C@@H]1[C@@H]([C@]2(C(=O)C[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 QOLRLLFJMZLYQJ-LOBDNJQFSA-N 0.000 claims 1
• OXLGJTRVVNGJRK-UHFFFAOYSA-N Hecogenin Natural products CC1CCC2(CC3CC4C5CCC6CC(O)CCC6(C)C5CC(=O)C4(C)C3C2C)OC1 OXLGJTRVVNGJRK-UHFFFAOYSA-N 0.000 claims 1
• WVVOBOZHTQJXPB-UHFFFAOYSA-N N-anilino-N-nitronitramide Chemical compound [N+](=O)([O-])N(NC1=CC=CC=C1)[N+](=O)[O-] WVVOBOZHTQJXPB-UHFFFAOYSA-N 0.000 claims 1
• UVLDESQWQRMYKD-UHFFFAOYSA-N Neobotogenin Natural products CC1C(C2(C(=O)CC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 UVLDESQWQRMYKD-UHFFFAOYSA-N 0.000 claims 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
• 229930182558 Sterol Natural products 0.000 claims 1
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
• CQODGVQBRIGKLJ-UHFFFAOYSA-L [Na+].[Na+].[O-]OOO[O-] Chemical compound [Na+].[Na+].[O-]OOO[O-] CQODGVQBRIGKLJ-UHFFFAOYSA-L 0.000 claims 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
• 150000001412 amines Chemical class 0.000 claims 1
• 238000004458 analytical method Methods 0.000 claims 1
• HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 claims 1
• 230000031709 bromination Effects 0.000 claims 1
• 238000005893 bromination reaction Methods 0.000 claims 1
• 125000001246 bromo group Chemical group Br* 0.000 claims 1
• 239000007795 chemical reaction product Substances 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 claims 1
• NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims 1
• RCTFHBWTYQOVGJ-UHFFFAOYSA-N chloroform;dichloromethane Chemical compound ClCCl.ClC(Cl)Cl RCTFHBWTYQOVGJ-UHFFFAOYSA-N 0.000 claims 1
• 239000011651 chromium Substances 0.000 claims 1
• 150000001844 chromium Chemical class 0.000 claims 1
• XZQOHYZUWTWZBL-UHFFFAOYSA-L chromium(ii) bromide Chemical group [Cr+2].[Br-].[Br-] XZQOHYZUWTWZBL-UHFFFAOYSA-L 0.000 claims 1
• UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims 1
• 229940125782 compound 2 Drugs 0.000 claims 1
• 239000010949 copper Substances 0.000 claims 1
• 239000002178 crystalline material Substances 0.000 claims 1
• 230000018044 dehydration Effects 0.000 claims 1
• 238000006297 dehydration reaction Methods 0.000 claims 1
• 238000007269 dehydrobromination reaction Methods 0.000 claims 1
• 238000006704 dehydrohalogenation reaction Methods 0.000 claims 1
• CPELXLSAUQHCOX-DYCDLGHISA-N deuterium bromide Chemical compound [2H]Br CPELXLSAUQHCOX-DYCDLGHISA-N 0.000 claims 1
• 238000010790 dilution Methods 0.000 claims 1
• 239000012895 dilution Substances 0.000 claims 1
• YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
• 238000004821 distillation Methods 0.000 claims 1
• 229940079593 drug Drugs 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 238000001035 drying Methods 0.000 claims 1
• DNVPQKQSNYMLRS-SOWFXMKYSA-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-SOWFXMKYSA-N 0.000 claims 1
• 239000000706 filtrate Substances 0.000 claims 1
• 238000001914 filtration Methods 0.000 claims 1
• 239000012467 final product Substances 0.000 claims 1
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
• 239000012362 glacial acetic acid Substances 0.000 claims 1
• 238000003306 harvesting Methods 0.000 claims 1
• 238000010438 heat treatment Methods 0.000 claims 1
• 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
• 238000009434 installation Methods 0.000 claims 1
• 150000002500 ions Chemical class 0.000 claims 1
• 238000002955 isolation Methods 0.000 claims 1
• 239000012280 lithium aluminium hydride Substances 0.000 claims 1
• XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 1
• 229910052808 lithium carbonate Inorganic materials 0.000 claims 1
• ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 claims 1
• 239000011777 magnesium Substances 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 239000000463 material Substances 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• 235000010755 mineral Nutrition 0.000 claims 1
• 239000011707 mineral Substances 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
• 229910052757 nitrogen Inorganic materials 0.000 claims 1
• 239000012044 organic layer Substances 0.000 claims 1
• 239000003960 organic solvent Substances 0.000 claims 1
• 235000006408 oxalic acid Nutrition 0.000 claims 1
• DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 claims 1
• 239000002245 particle Substances 0.000 claims 1
• 229910052698 phosphorus Inorganic materials 0.000 claims 1
• 239000011574 phosphorus Substances 0.000 claims 1
• DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 1
• 239000002244 precipitate Substances 0.000 claims 1
• 238000001556 precipitation Methods 0.000 claims 1
• 229960003387 progesterone Drugs 0.000 claims 1
• 239000000186 progesterone Substances 0.000 claims 1
• 150000003839 salts Chemical class 0.000 claims 1
• 238000000926 separation method Methods 0.000 claims 1
• 235000009518 sodium iodide Nutrition 0.000 claims 1
• 150000003432 sterols Chemical class 0.000 claims 1
• 235000003702 sterols Nutrition 0.000 claims 1
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