Solid phase urea synthesis: An efficient and direct conversion of Fmoc-protected amines to ureas

Authors
Chong, PY Petillo, PA
Citation
Py. Chong et Pa. Petillo, Solid phase urea synthesis: An efficient and direct conversion of Fmoc-protected amines to ureas, TETRAHEDR L, 40(24), 1999, pp. 4501-4504
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
24
Year of publication
1999
Pages
4501 - 4504
Database
ISI
SICI code
0040-4039(19990611)40:24<4501:SPUSAE>2.0.ZU;2-0
Abstract
An efficient "one-pot" conversion of Fmoc-protected amino acids to the urea s in the solid phase is described. This methodology uses MeSiCl3 in the pre sence of Et3N to cleave Fmoc-protected amines directly to their isocyanates . This transformation has been demonstrated on some Fmoc-protected amino ac ids. Trapping of the resin-bound isocyanate by the addition of amines gener ates the desired amino acid ureas in high HPLC purities. (C) 1999 Elsevier Science Ltd. All rights reserved.