Carbonyldiimidazole (CDI) Mediated Synthesis of Nα-Protected Amino Acid Azides: Application to the One-pot Preparation of Ureidopeptides

Title: Carbonyldiimidazole (CDI) Mediated Synthesis of Nα-Protected Amino Acid Azides: Application to the One-pot Preparation of Ureidopeptides

Volume: 18 Issue: 11

Author(s): B. Vasantha, T. M. Vishwanatha and Vommina V. Sureshbabu

Affiliation:

Keywords: Acyl azide, CDI, one-pot reaction, ureidopeptides, cycloaddition reactions, HIV-1 protease inhibitors, Leuch's anhydride, isocyanates, diphenylphosphoryl azide (DPPA), HBTU, EDC, MAPI, Buchi model, HR-MSAcyl azide, CDI, one-pot reaction, ureidopeptides, cycloaddition reactions, HIV-1 protease inhibitors, Leuch's anhydride, isocyanates, diphenylphosphoryl azide (DPPA), HBTU, EDC, MAPI, Buchi model, HR-MS

Abstract: Synthesis of Nα-protected amino acyl azides starting from corresponding acids via the carbonyldiimidazole (CDI) activation is described. The protocol is extended for a one-pot preparation of ureido peptides that circumvents the isolation of acyl azide and isocyanate intermediates. The reaction was accomplished without using any additives and base. The protocol is simple, clean, high yielding and free from racemization.

Cite this article as:

Vasantha B., M. Vishwanatha T. and V. Sureshbabu Vommina, Carbonyldiimidazole (CDI) Mediated Synthesis of Nα-Protected Amino Acid Azides: Application to the One-pot Preparation of Ureidopeptides, Protein & Peptide Letters 2011; 18 (11) . https://dx.doi.org/10.2174/092986611797200922