Efficient and simple one-pot conversion of resin-bound N-Fmoc amino acids and dipeptides into N-Boc derivatives

Ricardo L E Furlán,Ernesto G Mata,Paul Krapcho

doi:10.3998/ark.5550190.0004.a05

Abstract

Wang resin bound N-fluorenylmethoxycarbonyl (Fmoc) amino acids and dipeptides were efficiently converted into the corresponding N-tert-butoxycarbonyl (Boc) derivatives using two different “one-pot” procedures: potassium fluoride / di-tert-butyl carbonate and potassium fluoride / tert-butyl S-(4,6-dimethylpyrimidin-2-yl) thiolcarbonate.

Highlights

Despite the proliferation of protecting groups, functional group incompatibility remains a key issue in synthetic organic chemistry.[1]
We describe the efficient one-pot conversion of Wang resin bound N
Transprotection reactions were carried out combining a base and a tert-butoxycarbonylating reagent

Summary

Introduction

Despite the proliferation of protecting groups, functional group incompatibility remains a key issue in synthetic organic chemistry.[1]. Fmoc amino acids and dipeptides into the corresponding N-Boc derivatives.[16] We carried out the solid-phase transprotection of Fmoc-Phe-Wang resin using the combination potassium fluoride / di-tert-butyl dicarbonate in DMF.

Results

Conclusion