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...
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| Published in: | Tetrahedron letters Vol. 43; no. 18; pp. 3443 - 3445 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Ltd
29-04-2002
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| Abstract | 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.
Graphic |
|---|---|
| AbstractList | 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.
Graphic |
| Author | Sachinvala, Navzer D. Vasilevich, Natalya I. Maskos, Karol Coy, David H. |
| Author_xml | – sequence: 1 givenname: Natalya I. surname: Vasilevich fullname: Vasilevich, Natalya I. email: nvasile@tulane.edu organization: Peptide Research Laboratory, Tulane Health Sciences Center, 1430 Tulane Avenue, SL12, New Orleans, LA 70112, USA – sequence: 2 givenname: Navzer D. surname: Sachinvala fullname: Sachinvala, Navzer D. organization: Southern Regional Research Center, USDA-ARS, 1100 Robert E. Lee Blvd., New Orleans, LA 70124, USA – sequence: 3 givenname: Karol surname: Maskos fullname: Maskos, Karol organization: Coordinated Instrumentation Facility, Tulane University, 605 Lindy Boggs Building, New Orleans, LA 70118, USA – sequence: 4 givenname: David H. surname: Coy fullname: Coy, David H. organization: Peptide Research Laboratory, Tulane Health Sciences Center, 1430 Tulane Avenue, SL12, New Orleans, LA 70112, USA |
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| Cites_doi | 10.1111/j.1749-6632.1965.tb54077.x 10.1021/jo990092e 10.1016/S0040-4039(00)85958-4 10.1021/ja00052a088 10.1021/jm00281a032 10.1021/ja00275a008 10.1073/pnas.95.18.10836 10.1021/ja00034a083 10.1021/jm00263a044 10.1016/0006-291X(83)91225-1 10.1021/ja00295a052 10.1021/ja00268a061 10.1016/S0140-6736(80)92721-X 10.1002/j.1552-4604.1998.tb04397.x 10.1016/S0040-4039(99)02353-9 10.3109/10799899909036664 10.1016/S0955-3886(00)00089-8 |
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| Keywords | O-succinimidyl carbamate N-( O-carbamoyl)-succinmonoamides ureas N-acyl- O-carbamoyl hydroxylamine derivatives di- N-hydroxysuccinimidyl carbonate |
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| Snippet | N-Monoalkyl-
O-succinimidyl carbamates reacted with primary and secondary amines to produce ureas. However,
N,
N-dialkyl-
O-succinimidyl carbamates reacted... |
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| SubjectTerms | di- N-hydroxysuccinimidyl carbonate N-( O-carbamoyl)-succinmonoamides N-acyl- O-carbamoyl hydroxylamine derivatives O-succinimidyl carbamate ureas |
| Title | Selective conversion of O-succinimidyl carbamates to N-( O-carbamoyl)-succinmonoamides and ureas |
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