BE572021A

BE572021A -

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Publication number: BE572021A
Authority: BE; Belgium
Prior art keywords: steroid; solution; keto; chlorine; recovered
Prior art date

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English (en)

French (fr)

Publication of BE572021A publication Critical patent/BE572021A/fr

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238000000034 method Methods 0.000 claims description 41
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
239000000460 chlorine Substances 0.000 claims description 25
229910052801 chlorine Inorganic materials 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 17
230000002378 acidificating effect Effects 0.000 claims description 13
150000003431 steroids Chemical class 0.000 claims description 13
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
230000001590 oxidative effect Effects 0.000 claims description 9
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 6
KVUXYQHEESDGIJ-UHFFFAOYSA-N 10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,16-diol Chemical compound C1CC2CC(O)CCC2(C)C2C1C1CC(O)CC1(C)CC2 KVUXYQHEESDGIJ-UHFFFAOYSA-N 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 4
239000004380 Cholic acid Substances 0.000 claims description 4
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 4
229960002471 cholic acid Drugs 0.000 claims description 4
235000019416 cholic acid Nutrition 0.000 claims description 4
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 4
239000001632 sodium acetate Substances 0.000 claims description 4
235000017281 sodium acetate Nutrition 0.000 claims description 4
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 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 15
239000007858 starting material Substances 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 12
239000012362 glacial acetic acid Substances 0.000 description 10
239000000047 product Substances 0.000 description 9
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
229940040526 anhydrous sodium acetate Drugs 0.000 description 4
239000013078 crystal Substances 0.000 description 4
-1 hydroxy steroids Chemical class 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
239000012047 saturated solution Substances 0.000 description 4
HVGODGFJIFEJFW-JHEPDOOTSA-N (8S,9S,10R,13S,14S,17R)-5,6-dibromo-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-ol Chemical compound BrC12C(C[C@H]3[C@@H]4CC([C@@H]([C@]4(CC[C@@H]3[C@]2(CCCC1)C)C)[C@H](C)CCCC(C)C)O)Br HVGODGFJIFEJFW-JHEPDOOTSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
229960002997 dehydrocholic acid Drugs 0.000 description 2
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
SCGRTBFTNHXGPL-HAEFCYFZSA-N (4R)-4-[(3R,8R,9S,10S,12S,13R,14S,17R)-3-acetyloxy-12-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid Chemical compound C(C)(=O)O[C@H]1CC2CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(=O)O)C)[C@]4([C@H](C[C@@H]3[C@]2(CC1)C)O)C SCGRTBFTNHXGPL-HAEFCYFZSA-N 0.000 description 1
MLLXWRSMWXSEBS-DMINGUACSA-N (5S,8S,9S,10S,13S,14S)-7-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound OC1[C@@H]2[C@H](CC[C@@]3(CCC[C@H]32)C)[C@]3(CCC(C[C@@H]3C1)=O)C MLLXWRSMWXSEBS-DMINGUACSA-N 0.000 description 1
QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 description 1
ZDUVZJUTJOBJHS-LYRWWGFJSA-N (8s,9s,10s,13s,14s,17s)-17-(2-hydroxyacetyl)-10,13-dimethyl-2,4,5,6,7,8,9,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-3,11-dione Chemical compound C1C(=O)CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC21 ZDUVZJUTJOBJHS-LYRWWGFJSA-N 0.000 description 1
XNTYYYINMGRBQW-ZEZONBOOSA-N 3,12-Diketocholanic acid Chemical compound C([C@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)C(=O)C1 XNTYYYINMGRBQW-ZEZONBOOSA-N 0.000 description 1
OHXPGWPVLFPUSM-KLRNGDHRSA-N 3,7,12-trioxo-5beta-cholanic acid Chemical compound C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C OHXPGWPVLFPUSM-KLRNGDHRSA-N 0.000 description 1
XMRPGKVKISIQBV-BJMCWZGWSA-N 5alpha-pregnane-3,20-dione Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 XMRPGKVKISIQBV-BJMCWZGWSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
QORWWBHJCOMMST-DIEDPJQWSA-N COC(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](CC[C@]4(C)[C@H]3C[C@@H]([C@]12C)O)OCC1=CC=CC=C1)=O Chemical compound COC(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](CC[C@]4(C)[C@H]3C[C@@H]([C@]12C)O)OCC1=CC=CC=C1)=O QORWWBHJCOMMST-DIEDPJQWSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
DGABKXLVXPYZII-CDONHWFASA-N hyodeoxycholic acid Chemical compound C1([C@@H](O)C2)C[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 DGABKXLVXPYZII-CDONHWFASA-N 0.000 description 1
VCWDOHJFKGOMRJ-ATSXVDLPSA-N methyl (4r)-4-[(8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,12-dioxo-2,4,5,6,7,8,9,11,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)C(=O)C2 VCWDOHJFKGOMRJ-ATSXVDLPSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
235000021395 porridge Nutrition 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
238000002360 preparation method Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000009738 saturating Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1