NO126618B - - Google Patents

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Publication number: NO126618B
Authority: NO; Norway
Prior art keywords: acetate; chromium; hydroxy; bromo; gave
Prior art date: 1964-01-21

Application number

NO00156081A

Other languages

English (en)

Norwegian (no)

Inventor

N Of Massachusetts

Original Assignee

Res Inst Medicine Chem

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.)

1964-01-21

Filing date

1964-12-21

Publication date

1973-03-05

1964-12-21 Application filed by Res Inst Medicine Chem filed Critical Res Inst Medicine Chem

1973-03-05 Publication of NO126618B publication Critical patent/NO126618B/no

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WDNIVTZNAPEMHF-UHFFFAOYSA-N acetic acid;chromium Chemical compound [Cr].CC(O)=O.CC(O)=O WDNIVTZNAPEMHF-UHFFFAOYSA-N 0.000 claims description 26
238000000034 method Methods 0.000 claims description 20
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 claims description 19
-1 bromine steroid Chemical class 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000000463 material Substances 0.000 claims description 11
239000003638 chemical reducing agent Substances 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 9
UZEDIBTVIIJELN-UHFFFAOYSA-N chromium(2+) Chemical class [Cr+2] UZEDIBTVIIJELN-UHFFFAOYSA-N 0.000 claims description 8
150000003573 thiols Chemical class 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 claims description 3
JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
150000001838 cholestanes Chemical class 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 50
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 37
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
229960002899 hydroxyprogesterone Drugs 0.000 description 19
239000001569 carbon dioxide Substances 0.000 description 18
229910002092 carbon dioxide Inorganic materials 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
150000003431 steroids Chemical class 0.000 description 17
238000004587 chromatography analysis Methods 0.000 description 15
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
239000000523 sample Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
239000000047 product Substances 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 9
JMSRBKPMLUGHCR-UHFFFAOYSA-N bromohydrin Chemical compound BrC[C]1CO1 JMSRBKPMLUGHCR-UHFFFAOYSA-N 0.000 description 8
238000007256 debromination reaction Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
239000000203 mixture Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000000605 extraction Methods 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000012043 crude product Substances 0.000 description 5
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 5
125000000468 ketone group Chemical group 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
238000012546 transfer Methods 0.000 description 5
229910021554 Chromium(II) chloride Inorganic materials 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
229930194542 Keto Natural products 0.000 description 4
LRJOMUJRLNCICJ-JZYPGELDSA-N Prednisolone acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O LRJOMUJRLNCICJ-JZYPGELDSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
CMNUYDSETOTBDE-UHFFFAOYSA-N 1-benzyl-4h-pyridine-3-carboxamide Chemical compound C1=CCC(C(=O)N)=CN1CC1=CC=CC=C1 CMNUYDSETOTBDE-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
241000786363 Rhampholeon spectrum Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 3
239000008367 deionised water Substances 0.000 description 3
229910021641 deionized water Inorganic materials 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229960000890 hydrocortisone Drugs 0.000 description 3
229910021645 metal ion Inorganic materials 0.000 description 3
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 3
230000001603 reducing effect Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 3
NFHRNKANAAGQOH-UHFFFAOYSA-N triphenylstannane Chemical compound C1=CC=CC=C1[SnH](C=1C=CC=CC=1)C1=CC=CC=C1 NFHRNKANAAGQOH-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
125000004423 acyloxy group Chemical group 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
LJAOOBNHPFKCDR-UHFFFAOYSA-K chromium(3+) trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Cr+3] LJAOOBNHPFKCDR-UHFFFAOYSA-K 0.000 description 2
ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-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)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
239000000852 hydrogen donor Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
ZLUSCZLCHQSJRU-UHFFFAOYSA-N thallium(1+) Chemical compound [Tl+] ZLUSCZLCHQSJRU-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 2
UAPQJVJCJITJET-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 UAPQJVJCJITJET-UHFFFAOYSA-N 0.000 description 2
QGXBDMJGAMFCBF-XYQQMQERSA-N (1s,2s,7s,10r,11s,15s)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one Chemical compound C1C(O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-XYQQMQERSA-N 0.000 description 1
XCESQNFRBAHSGO-WRJHFWDFSA-N (8s,10s,13s,14s,17s)-17-acetyl-10,13-dimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)C3=CC[C@]4(C)[C@@H](C(=O)C)CC[C@H]4[C@@H]3CCC2=C1 XCESQNFRBAHSGO-WRJHFWDFSA-N 0.000 description 1
WNYLPFCKNQAAMB-PPUNREKOSA-N (8s,9s,10r,11s,13s,14s,16r,17r)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O WNYLPFCKNQAAMB-PPUNREKOSA-N 0.000 description 1
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 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910021556 Chromium(III) chloride Inorganic materials 0.000 description 1
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 description 1
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 description 1
CUDSBWGCGSUXDB-UHFFFAOYSA-N Dibutyl disulfide Chemical compound CCCCSSCCCC CUDSBWGCGSUXDB-UHFFFAOYSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
WBADDYWAKPDHJS-UHFFFAOYSA-N acetic acid ethene hexane Chemical compound CCCCCC.C(C)(=O)O.C=C WBADDYWAKPDHJS-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
FAMUPMBATZGWOV-UHFFFAOYSA-M bromo(triphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Br)C1=CC=CC=C1 FAMUPMBATZGWOV-UHFFFAOYSA-M 0.000 description 1
238000006380 bromofluorination reaction Methods 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
XIIAYQZJNBULGD-LDHZKLTISA-N cholestane group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 description 1
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
235000007831 chromium(III) chloride Nutrition 0.000 description 1
239000011636 chromium(III) chloride Substances 0.000 description 1
239000007799 cork Substances 0.000 description 1
229960004544 cortisone Drugs 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
239000000386 donor Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000003944 halohydrins Chemical class 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
229960002800 prednisolone acetate Drugs 0.000 description 1
229960004618 prednisone Drugs 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
238000012545 processing Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
150000003254 radicals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B31/00—Reduction in general
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

NO00156081A 1964-01-21 1964-12-21 NO126618B (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2631/64A GB1096942A (en)	1964-01-21	1964-01-21	Dehalogenation process

Publications (1)

Publication Number	Publication Date
NO126618B true NO126618B (fi)	1973-03-05

Family

ID=9742960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO00156081A NO126618B (fi)	1964-01-21	1964-12-21

Country Status (11)

Country	Link
US (1)	US3480622A (fi)
BE (1)	BE658068A (fi)
CH (1)	CH481030A (fi)
DE (1)	DE1468900A1 (fi)
DK (1)	DK125706B (fi)
FR (1)	FR1426431A (fi)
GB (1)	GB1096942A (fi)
IL (1)	IL22647A (fi)
NL (2)	NL6500724A (fi)
NO (1)	NO126618B (fi)
SE (1)	SE320660B (fi)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1459861A (en) *	1973-06-21	1976-12-31	Pfizer	Process for 11a-dehalogenation of 11a-halotetracyclines
EP0054390B1 (en) *	1980-12-05	1984-07-25	The Upjohn Company	Dehalogenation of steroids
US4304727A (en) *	1980-12-05	1981-12-08	The Upjohn Company	9α-Debromination
JP2604842B2 (ja) *	1987-08-14	1997-04-30	ジ・アップジョン・カンパニー	改良された９α‐脱ハロゲン化方法
CN108069881B (zh) *	2016-11-08	2020-09-15	中国科学院生态环境研究中心	一种氯代多氟醚基磺酸类化合物的还原转化方法

0
- NL NL128202D patent/NL128202C/xx active
1964
- 1964-01-21 GB GB2631/64A patent/GB1096942A/en not_active Expired
- 1964-12-18 IL IL22647A patent/IL22647A/en unknown
- 1964-12-21 NO NO00156081A patent/NO126618B/no unknown
1965
- 1965-01-08 BE BE658068D patent/BE658068A/xx unknown
- 1965-01-14 FR FR1887A patent/FR1426431A/fr not_active Expired
- 1965-01-19 CH CH71065A patent/CH481030A/de not_active IP Right Cessation
- 1965-01-20 NL NL6500724A patent/NL6500724A/xx unknown
- 1965-01-20 DK DK32065AA patent/DK125706B/da unknown
- 1965-01-20 SE SE712/65A patent/SE320660B/xx unknown
- 1965-01-21 DE DE1965R0039700 patent/DE1468900A1/de active Granted
1967
- 1967-05-08 US US636636A patent/US3480622A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
GB1096942A (en)	1967-12-29
BE658068A (fi)	1965-04-30
NL128202C (fi)
FR1426431A (fr)	1966-01-28
IL22647A (en)	1968-12-26
NL6500724A (fi)	1965-07-22
US3480622A (en)	1969-11-25
CH481030A (de)	1969-11-15
DE1468900A1 (de)	1969-01-09
DK125706B (da)	1973-03-26
SE320660B (fi)	1970-02-16

Publication	Publication Date	Title
NO156081B (no)	1987-04-13	Anordning til stramming av en ankerline.
NO131119B (fi)	1974-12-30
DK147735B (da)	1984-11-26	Analogifremgangsmaade til fremstilling af 3-oxo-androst-4-en-17beta-thiocarboxylsyreestere
NO148662B (no)	1983-08-15	Haarkondisjoneringssjampo.
JPH035400B2 (fi)	1991-01-25
NO126618B (fi)	1973-03-05
GB1603566A (en)	1981-11-25	Steroidal naphthalenes
Christensen et al.	1960	The Partial Synthesis of 12α-Methyl-11-dehydrocorticosterone
Bowers et al.	1959	Steroids. CIX. 1 Studies in Nitro Steroids. Part 1. The Synthesis of 6α-and 6β-Nitrotestosterone and 6α-and 6β-Nitroprogesterone2
NO146682B (no)	1982-08-09	Tetningsmatel for isolerte roerledninger
Kabat	1995	Synthesis of Digitoxigenin from 3. beta.-Acetoxyandrost-5-en-17-one. Construction of a Suitably Functionalized Pregnane Side Chain via Presumed Allene Oxide Intermediate
Pines	2004	The Merck bile acid cortisone process: the next-to-last word
US3787396A (en)	1974-01-22	17-hydroxy-7-(lower alkoxy)carbonyl-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid ypsilon-lactones and congeners
US2777843A (en)	1957-01-15	Preparation of 4-pregnen-17alpha-ol-3, 20-dione
Clarke	1960	Some Reactions of 2-Hydroxytestosterone and its Diacetate. I
CN103421070A (zh)	2013-12-04	一种改进的孕甾烯类化合物c21-乙酰氧基化方法
Shapiro et al.	1966	3β-hydroxy-1, 5-bisdehydro steroids
DK142992B (da)	1981-03-09	Fremgangsmaade til fremstilling af steroid-17-spirolactoner eller metlsalte af den tilsvarende hydroxycarboxylsyre af den 6,7-umaettede forbindelse
Djerassi et al.	1954	Terpenoids. VII. 1 Experiments in the Glycyrrhetic Acid Series
US3298941A (en)	1967-01-17	Photochemical process for rearranging organic hypohalite and nitrite compounds
US3100204A (en)	1963-08-06	Haloethisterone compounds
Shapiro et al.	1969	Synthesis and progestational activity of some 1, 2. alpha.-cyclomethylene-16-methylene progesterone derivatives
US2968662A (en)	1961-01-17	6-halo-6-dehydro derivatives of 11-oxygenated-9 alpha-haloprogesterones
US4220588A (en)	1980-09-02	Chemical processes
US2860149A (en)	1958-11-11	Process for the saponification of 21-esters of 20-keto pregnanes