Effect of the Position of Reaction-Site in Amphipathic-Type Thioester in Aqueous Amidation Reaction

Abstract

Amphipathic-type thioesters CH 3 (CH 2 ) m COS(CH 2 ) n COONa (m + n = 12) were synthesized and their reaction with various alkylamines was examined. Compounds having thioester moiety close to carboxylate (m = 10, n = 2) afforded the corresponding amides in good yields, while the substrate having thioester moiety distant from carboxylate (m = 2, n = 10) afforded the amides in relatively low yield. In all cases, the difference in yield due to the chain length of amine was not observed. The results indicated that the reaction took place effectively near the surface of micelle. However, the reaction was found to occur not only on micelle surface but also in solution.