Efficient Synthesis of N-Benzyloxycarbonyl-2-aminoalkanesulfonyl Chlorides with Functionalized Side Chains

Hassane Abdellaoui; Xingpeng Chen; Jiaxi Xu

doi:10.1055/s-0036-1588706

Synthesis, Table of Contents

Synthesis 2017; 49(10): 2250-2256
DOI: 10.1055/s-0036-1588706

paper

Efficient Synthesis of N-Benzyloxycarbonyl-2-aminoalkanesulfonyl Chlorides with Functionalized Side Chains

Hassane Abdellaoui

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China Email: hasabdel89@hotmail.fr Email: chenxp7613@163.com Email: jxxu@mail.buct.edu.cn

,

Xingpeng Chen

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China Email: hasabdel89@hotmail.fr Email: chenxp7613@163.com Email: jxxu@mail.buct.edu.cn

,

Jiaxi Xu*

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China Email: hasabdel89@hotmail.fr Email: chenxp7613@163.com Email: jxxu@mail.buct.edu.cn

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Abstract

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Abstract

N-Benzyloxycarbonyl (Cbz)-protected 2-aminoalkanesulfonyl chlorides are useful building blocks for the synthesis of sulfonopeptides, which are receptor ligands and enzyme inhibitors, and are prepared by the coupling reaction of N-protected aminoalkanesulfonyl chlorides with amino acid or peptide esters. Various N-Cbz-protected 2-aminoalkanesulfonyl chlorides with functionalized side chains were synthesized through the radical addition of different xanthates to benzyl N-allylcarbamate and subsequent oxidative chlorination with tert-butyl hypochlorite under neutral conditions. A mechanism for the oxidative chlorination is proposed. This is a useful and convenient strategy for the synthesis of N-Cbz-protected 2-aminoalkanesulfonyl chlorides with diverse functionalized side-chains.

Key words

oxidative chlorination - radical reaction - sulfonyl chlorides - xanthate - aminoalkanesulfonyl chloride

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