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

[ Vol. 18 , Issue. 11 ]

Author(s):

B. Vasantha, T. M. Vishwanatha and Vommina V. Sureshbabu   Pages 1093 - 1098 ( 6 )

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.

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

Affiliation:

Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore -560 001, India.



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