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Synthesis 2013; 45(19): 2727-2736
DOI: 10.1055/s-0033-1339488
DOI: 10.1055/s-0033-1339488
paper
An Efficient Synthesis of Nα-Protected Amino and Peptide Acid Aryl Amides via Iodine-Mediated Oxidative Acylation of Nα-Protected Amino and Peptide Thioacids
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Publication History
Received: 27 May 2013
Accepted after revision: 08 July 2013
Publication Date:
06 August 2013 (online)
Abstract
Thioacids derived from N-protected amino or dipeptide and tripeptide acids undergo facile N-acylation with aromatic amines to afford N-protected amino or peptide aryl amides in good to excellent yields and enantiopurities. The method also furnishes difficult-to-prepare N-Fmoc amino acid 4-nitroanilides in good yields. This simple oxidative Nα-acylation of thioacids with aromatic amines proceeds in the presence of iodine, 1-hydroxybenzotriazole and N,N-diisopropylethylamine at room temperature in tetrahydrofuran.
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