ω-Aryloxy Analogs of Prostamides

Abstract

Acylation of cloprostenol with acetic anhydride in pyridine, followed by treatment of the exhaustive acetylation product with water, gave 9,11,15-triacetoxy derivative whose reaction with 1,1′-carbonyldiimidazole afforded the corresponding imidazolide. The subsequent condensation with 2-aminoethanol and removal of acetate protecting group lead to the formation of N-(2-hydroxyethyl) cloprostenol amide. Analogous N-ethyl amide was synthesized by reaction of cloprostenol methyl ester with aqueous ethylamine.