BE491355A

BE491355A -

Info

Publication number: BE491355A
Authority: BE; Belgium
Prior art keywords: parts; steroids; volume; solution; ether
Prior art date

Application number

Other languages

English (en)

French (fr)

Publication of BE491355A publication Critical patent/BE491355A/fr

Links

238000000034 method Methods 0.000 claims description 13
150000003431 steroids Chemical class 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 9
238000010494 dissociation reaction Methods 0.000 claims description 6
230000005593 dissociations Effects 0.000 claims description 6
238000005984 hydrogenation reaction Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229910052987 metal hydride Inorganic materials 0.000 claims description 4
150000004681 metal hydrides Chemical class 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
239000003638 reducing agent Substances 0.000 claims description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
229910052796 boron Inorganic materials 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
238000002844 melting Methods 0.000 description 27
HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 16
OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 16
238000006722 reduction reaction Methods 0.000 description 16
238000003756 stirring Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000000155 melt Substances 0.000 description 11
239000000126 substance Substances 0.000 description 11
125000003700 epoxy group Chemical group 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
239000004593 Epoxy Substances 0.000 description 8
SRTHRWZAMDZJOS-UHFFFAOYSA-N Lithium hydride Chemical compound [H-].[Li+] SRTHRWZAMDZJOS-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
229910052782 aluminium Inorganic materials 0.000 description 7
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
230000000875 corresponding Effects 0.000 description 5
150000004702 methyl esters Chemical class 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
238000006640 acetylation reaction Methods 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
229920000647 polyepoxide Polymers 0.000 description 3
229940088597 Hormone Drugs 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
230000001919 adrenal Effects 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910010277 boron hydride Inorganic materials 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
238000011097 chromatography purification Methods 0.000 description 2
KLDBIFITUCWVCC-UHFFFAOYSA-N diborane(6) Chemical compound [H]B1([H])[H]B([H])([H])[H]1 KLDBIFITUCWVCC-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
239000005556 hormone Substances 0.000 description 2
150000002440 hydroxy compounds Chemical class 0.000 description 2
-1 lithium aluminum Chemical compound 0.000 description 2
230000001264 neutralization Effects 0.000 description 2
YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Chemical compound [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 2
BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 2
MQSSTQLJJOVNQF-KWHXHVTNSA-N (3S,5S,8R,9S,10S,13S,14S,17R)-17-[(1R)-1,2-dihydroxyethyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)[C@H](O)CO)[C@@H]4[C@@H]3CC[C@H]21 MQSSTQLJJOVNQF-KWHXHVTNSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
UIMGHSAOLFTOBF-UHFFFAOYSA-N 10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound C1CC2=CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 UIMGHSAOLFTOBF-UHFFFAOYSA-N 0.000 description 1
229960000583 Acetic Acid Drugs 0.000 description 1
244000304921 Charybdis maritima Species 0.000 description 1
XIIAYQZJNBULGD-LDHZKLTISA-N Cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 description 1
VQWFNAGFNGABOH-UHFFFAOYSA-K Chromium(III) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
240000001879 Digitalis lutea Species 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N N-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N Peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
101710025312 SLC51A Proteins 0.000 description 1
102100002996 TAC1 Human genes 0.000 description 1
101700065588 TAC1 Proteins 0.000 description 1
101700075346 TKNB Proteins 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
238000007792 addition Methods 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
125000002723 alicyclic 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
150000001340 alkali metals Chemical class 0.000 description 1
239000003088 amphibian venom Substances 0.000 description 1
235000020127 ayran Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004432 carbon atoms Chemical group C* 0.000 description 1
230000003177 cardiotonic Effects 0.000 description 1
230000003197 catalytic Effects 0.000 description 1
GGCLNOIGPMGLDB-GYKMGIIDSA-N cholest-5-en-3-one Chemical compound C1C=C2CC(=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 GGCLNOIGPMGLDB-GYKMGIIDSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003163 gonadal steroid hormone Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000009434 installation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000004072 triols Chemical class 0.000 description 1