Conversion of O-succinimidyl carbamates to N-(O-carbamoyl)-succinmonoamides and ureas:: effects of N-substituents and reaction conditions on the reaction pathway

Whereas N-monoalkyl-O-succinimidyl carbamates reacted with primary and secondary amines to produce Only ureas, N,N-dialkyl-O-succinimidyl carbamates reacted with primary and secondary amines to produce N-(O-carbamoyl)-succinmonoamides. N-Alkyl-N-aryl-O-succinimidyl carbamates under the same condition led to Mixture of both products. The effects of N-substituents and reaction conditions On O-succinimidyl carbamates conversion are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.