Synthesis of Optically Active 2- (4- (2-Thienylcarbonyl) -phenyl) propionic Acid Labeled with Deuterium

Abstract

2- (4- (2-Thienylcarbonyl) phenyl) propionic acid (suprofen), an anti-inflammatory agent, was labeled with multiple-deuterium for the purpose of investigating the metabolism in man and animals by the ion cluster technique. Racemic suprofen-d₄ was prepared by ten-step synthesis from bromobenzene-d₅ in a 32% yield, and its deuterium content was 99 atom%. This racemic suprofen-d₄was resolved by use of an optically active a-methylbenzylamine, resulting that optically active suprofen-d₄ was obtained in a 11% yield and was 96.5 atom% D. On the other hand, suprofen-d₇ (99 atom% D) was obtained by five-step synthesis from toluene-d₈ and methyl-d₃iodide in a 24% yield.