A novel solid-phase synthesis of di- and trisubstituted N-acyl ureas |
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Authors: | Jacob RavnMichael Ankersen Mikael BegtrupJesper F. Lau |
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Affiliation: | a Medicinal Chemistry, Novo Nordisk A/S, Novo Nordisk Park, DK-2760 Maaloev, Denmark b The Danish University of Pharmaceutical Sciences, Universitetsparken 2, DK-2100 Copenhagen, Denmark |
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Abstract: | 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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