Further studies on the use of the thallium salt of N-hydroxysuccinimide for the preparation of succinimidyl esters

Abstract

An efficient preparation of four alkyl (ethyl, tert-butyl, p-nitrobenzyl, trichloroethyl) succinimidyl carbonates from the thallium salt of N-hydroxysuccinimide and corresponding chloroformates is described. The general utility of trichloroethyl succinimidyl carbonate is demonstrated by its reaction with glycine to give trichloroethoxycarbonylglycine. The preparation of succinimidyl esters of numerous fatty acids using the thallium salt of N-hydroxysuccinimide and the corresponding acid chlorides is described. The advantage of this method over the N,N′-dicyclohexylcarbodiimide method for the preparation of these esters is demonstrated. Succinimidyl p-toluenesulfonate and chloroacetate were also prepared.