Acetic Anhydride → HCID 15580497, compound

Participants

Reaction Steps

A mixture of 156 mg of (8R,11R,12S,15R,5Z,13E)-15-hydroxy-11,16,16-trimethyl-9-oxoprosta-5,13-dien-1-oic acid, 100 mg of acetic, anhydride, 21 mg of 4-(dimethylamino)pyridine, and 2 ml of triethylamine was stirred at room temperature under a positive nitrogen atmosphere. After 16 hr, the reaction mixture was partitioned between ethyl acetate-water and the organic layer separated, dried (MgSO4), and condensed by rotary evaporation. The residual material was purified by chromatography over Sephadex LH-20 (hydroxypropylated beaded dextran) using chloroform/hexane (3:2) as the eluant to yield 112 mg (65%) of (8R,11R,12S,15R,5Z,13E)-15-acetyloxy-11,16,16-trimethyl-9-oxoprosta-5,13-dien-1-oic acid. [α]D25 -78.52 (CHCl3, c 1.02).

Provenance & Evidence