Chenodeoxycholic Acid → Methyl cholate

HRID 1973708Notes

Reaction equation

[CH3:1][C@@H]([C@@H]1[C@@]2(C)CC[C@@H]3[C@@]4(C)CC[C@@H](O)C[C@H]4C[C@@H](O)[C@H]3[C@@H]2CC1)CCC(O)=O.[CH3:29][C@@H:30]([C@@H:36]1[C@@:40]2([CH3:57])[C@@H:41]([OH:56])[CH2:42][C@@H:43]3[C@@:48]4([CH3:54])[CH2:49][CH2:50][C@@H:51]([OH:53])[CH2:52][C@H:47]4[CH2:46][C@@H:45]([OH:55])[C@H:44]3[C@@H:39]2[CH2:38][CH2:37]1)[CH2:31][CH2:32][C:33]([OH:35])=[O:34]>>[CH3:29][C@@H:30]([C@@H:36]1[C@@:40]2([CH3:57])[C@@H:41]([OH:56])[CH2:42][C@@H:43]3[C@@:48]4([CH3:54])[CH2:49][CH2:50][C@@H:51]([OH:53])[CH2:52][C@H:47]4[CH2:46][C@@H:45]([OH:55])[C@H:44]3[C@@H:39]2[CH2:38][CH2:37]1)[CH2:31][CH2:32][C:33]([O:35][CH3:1])=[O:34]

Participants

Reactant 2

HCID 10133Chenodeoxycholic Acid

HCID 221493Cholic Acid2×

Product 1

HCID 10960835Methyl cholate

Procedure

A process for preparing chenodeoxycholic acid from cholic acid comprising the steps of: (1) esterification of the acid group of the cholic acid to produce methyl cholate; (2) selective acetylation of the methyl cholate to produce methyl 3,7-diacetyl cholate; (3) mesylation of the methyl 3,7-diacetyl cholate to produce methyl 3,7-diacetyl-12-mesylcholate; (4) dehydromesylation of the methyl 3,7-diacetyl-12-mesylcholate by hexamethylphosphoric triamide in the presence of a weak base to produce methyl 3,7-diacetylchol-11-enate; (5) hydrogenation of the methyl 3,7-diacetylchol-11-enate to produce methyl diacetyl chenodeoxycholate; and (6) saponification of the methyl diacetyl chenodeoxycholate to produce chenodeoxycholic acid.

Sources & evidence

ORD record: ord-14a078bd3e86425a972feb47070ce38e
Source dataset: uspto-grants-1976_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03998859

Reaction notes

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