Efficient Synthesis of N-Fmoc-Aminoalkoxy Pentafluorophenyl Carbonates: Application for the Synthesis of Oligopeptidyl Carbamates

Abstract

N-Fmoc-β-Aminoalkoxy pentafluorophenyl carbonates have been synthesized through the reaction of N-Fmoc-β-aminoalkoxy carbonyl chloride with pentafluorophenol. The reaction was clean and high yielding, and the products have been fully characterized using infrared, NMR, and mass spectroscopy. Their utility as efficient building blocks for the preparation of N-Fmoc-oligopeptidyl carbamate esters and acids has been demonstrated. The method exemplifies a simple protocol for the efficient preparation of oligopeptidyl carbamates in solution phase.

Keywords:

• N-Fmoc-β-Aminoalkoxy carbonyl chlorides
• carbonates
• oligopeptidyl carbamates
• pentafluorophenol

ACKNOWLEDGMENT

We thank the Council of Scientific and Industrial Research (CSIR), New Delhi [Grant No. 01(2034)/06/EMR-II] for the financial support.