Preparation of N'-Succinimidyl Carboxylates with the Use of N, N'-Disuccinimidyl Oxalate (DSO)

Abstract

A method was devised for preparation of N-succinimidyl carboxylates (N-succinimidyl esters of fatty, benzoic and arylacetyl acids) using N, N'-disuccinimidyl oxalate (DSO). Reaction of acids with DSO in the presence of pyridine in acetonitrile gave the corresponding esters in good yields. N-Hydroxysuccinimide which was formed during the reactions and pyridine in the reaction mixtures could be easily removed by treatment with water. This method was compared with those previously reported using N, N'-dicyclohexylcarbodiimide (DCC) and N, N'-disuccinimidyl carbonate (DSC).