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

Chilakapati Madhu; T. M. Vishwanatha; Vommina V. Sureshbabu

doi:10.1055/s-0033-1339488

Synthesis, Table of Contents

Synthesis 2013; 45(19): 2727-2736
DOI: 10.1055/s-0033-1339488

paper

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

#109, Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560 001, India Fax: +91(80)22292848 Email: sureshbabuvommina@rediffmail.com Email: hariccb@gmail.com Email: hariccb@hotmail.com

,

T. M. Vishwanatha

#109, Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560 001, India Fax: +91(80)22292848 Email: sureshbabuvommina@rediffmail.com Email: hariccb@gmail.com Email: hariccb@hotmail.com

,

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 Fax: +91(80)22292848 Email: sureshbabuvommina@rediffmail.com Email: hariccb@gmail.com Email: hariccb@hotmail.com

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Abstract

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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 N^α-acylation of thioacids with aromatic amines proceeds in the presence of iodine, 1-hydroxybenzotriazole and N,N-diisopropylethylamine at room temperature in tetrahydrofuran.

Key words

thioacids - acylation - aryl amides - iodine

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References

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