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

Abstract 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.