Selective conversion of O-succinimidyl carbamates to N-(O-carbamoyl)-succinmonoamides and ureas

N-Monoalkyl-O-succinimidyl carbamates reacted with primary and secondary amines to produce ureas. However, N,N-dialkyl-O-succinimidyl carbamates reacted with primary and secondary amines, via succinimide ring opening, to afford N-(O-carbamoyl)-succinmonoamide derivatives. This ring-opening trend was also true with hydroxy and alkoxy nucleophiles. Herein, general methods for the synthesis and NMR characterization of N-(O-carbamoyl)-succinmonoamides are reported.