Sulfuric Acid → 3alpha-Hydroxy-7-oxo-5beta-cholan-24-oic acid methyl ester

HRID 591871

Reaktionsgleichung

Reaktionsgleichung von HRID 591871
CC[C@H:3]1[C@@H:16]([OH:17])[C@@H:15]2[C@H:10]([CH2:11][CH2:12][C@:13]3([CH3:28])[C@@H:20]([C@@H:21]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH3:22])[CH2:19][CH2:18][C@H:14]32)[C@:9]2([CH3:29])[C@H:4]1[CH2:5][C@H:6]([OH:30])[CH2:7][CH2:8]2.O[C@@H:32]1CC[C@@]2(C)[C@H](CC(=O)[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2[C@H](C)CCC(O)=O)C1.OS(O)(=O)=O>CO>[CH3:32][O:27][C:25](=[O:26])[CH2:24][CH2:23][C@H:21]([C@@H:20]1[C@:13]2([CH3:28])[C@H:14]([C@H:15]3[C@H:10]([CH2:11][CH2:12]2)[C@:9]2([CH3:29])[C@@H:4]([CH2:5][C@H:6]([OH:30])[CH2:7][CH2:8]2)[CH2:3][C:16]3=[O:17])[CH2:18][CH2:19]1)[CH3:22]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 4442627-Ketolithocholic acidHCID 447715Obeticholic Acid

Produkt 1

HCID 99310883alpha-Hydroxy-7-oxo-5beta-cholan-24-oic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The present invention relates to a process for preparing obeticholic acid Form 1, wherein reacting 3α-hydroxy-7-keto-5β-cholan-24-oic acid with CH3OH and H2SO4 to form 3α-hydroxy-7-keto-5β-cholan-24-oic acid methyl ester is heated for about 3 hours and the pH of the reaction mixture is adjusted with an aqueous basic solution to a pH-value of about 6.5 to about 8.0.

Quellen und Nachweise

ORD-Eintrag
ord-e2367bcf87e74690a5b7945bc7e79883
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238673B2

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