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A novel solid-phase synthesis of di- and trisubstituted N-acyl ureas

โœ Scribed by Jacob Ravn; Michael Ankersen; Mikael Begtrup; Jesper F. Lau

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
376 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A novel, mild method for the synthesis of di-and trisubstituted N-acyl ureas on solid support is described. Addition of carboxylic acids to a resin-bound carbimidoyl chloride gave, initially, an O-acyl isourea which subsequently rearranged to the corresponding N-acyl urea. Trisubstituted N-acyl ureas were assembled on a Wang resin from a wide range of Fmoc amino acids, secondary amines and carboxylic acids. Acid mediated cleavage yielded the products in good yields and excellent purities. In addition, the regioselective synthesis of disubstituted N-acyl ureas is demonstrated with four examples.

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