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

• Published in: Tetrahedron letters Vol. 43; no. 18; pp. 3443 - 3445
• Main Authors: Vasilevich, Natalya I., Sachinvala, Navzer D., Maskos, Karol, Coy, David H.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 29-04-2002
• Subjects: di- N-hydroxysuccinimidyl carbonate; N-( O-carbamoyl)-succinmonoamides; N-acyl- O-carbamoyl hydroxylamine derivatives; O-succinimidyl carbamate; ureas; O-succinimidyl carbamate; N-( O-carbamoyl)-succinmonoamides; ureas; N-acyl- O-carbamoyl hydroxylamine derivatives; di- N-hydroxysuccinimidyl carbonate
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(02)00554-3

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.
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