Microwave-induced organic reactions of bile acids: esterification, deformylation and deacetylation using mild reagents.
An efficient and convenient procedure for the esterification, deformylation, and deacetylation of bile acids is described. This is achieved by the addition of a catalytic amount of methanesulfonic acid or para-toluene sulfonic acid to a solution of bile acid in methanol in the domestic microwave oven. All these reactions were completed in the microwave oven within 1-3 min at 60% power (390 W) and the desired bile acids, namely trihydroxy-5 beta-cholestanoic acid, (23R)-3 alpha,7 alpha,23-trihydroxy-5 beta-cholan-24-oic acid, ursocholic acid and 7-ketolithocholic acid were isolated in 86-94% yield.
Dayal
B
B
Department of Medicine, UMDNJ-New Jersey Medical School, Newark, USA.
Rao
K
K
Salen
G
G
D000107:Acetylation; D001557:Benzenesulfonates / Q000494:pharmacology; D001647:Bile Acids and Salts / Q000737:chemistry*; D019826:Cholic Acid; D002793:Cholic Acids / Q000737:chemistry; D004951:Esterification; D007202:Indicators and Reagents; D008095:Lithocholic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D008698:Mesylates / Q000494:pharmacology; D008872:Microwaves; D015394:Molecular Structure
D001557:Benzenesulfonates; D001647:Bile Acids and Salts; D002793:Cholic Acids; D007202:Indicators and Reagents; D008698:Mesylates; C045880:methanesulfonic acid; C023020:7-ketolithocholic acid; D008095:Lithocholic Acid; D019826:Cholic Acid; C030712:ursocholic acid; C007036:cholanic acid; C029501:4-toluenesulfonic acid