An Efficient Synthesis of N^α-Protected Amino and Peptide Acid Aryl Amides via Iodine-Mediated Oxidative Acylation of N^α-Protected Amino and Peptide Thioacids

Chilakapati Madhu, T. M. Vishwanatha, Vommina V. Sureshbabu*

*#109, Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560 001, India, Email: sureshbabuvomminarediffmail.com

C. Madhu, T. M. Vishwanatha, V. V. Sureshbabu, Synthesis, 2013, 45, 2727-2736.

DOI: 10.1055/s-0033-1339488

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Abstract

Thioacids derived from N-protected amino or polypeptide acids undergo facile N-acylation with aromatic amines to afford aryl amides in good to excellent yields and enantiopurities in the presence of iodine, 1-hydroxybenzotriazole and N,N-diisopropylethylamine at room temperature. This oxidative N^α-acylation also furnishes difficult-to-prepare N-Fmoc amino acid 4-nitroanilides in good yields.

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Key Words

thioacids, acylation, amides, iodine

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ID: J66-Y2013