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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Research Article

Expeditious Preparation of N-Fmoc 2-Aminoethanesulfonyl Chlorides with Functionalized 1-Substituents

Author(s): Kheira Haiouani, Xingpeng Chen and Jiaxi Xu*

Volume 15 , Issue 2 , 2018

Page: [246 - 255] Pages: 10

DOI: 10.2174/1570179414666170821120705

Price: $65

Abstract

Aim and Objective: [(9H-Fluoren-9-yl)methoxy]carbonyl (Fmoc)-protected 2-aminoethanesulfonyl chlorides with various functionalized 1-substituents may be of use as building blocks for the Fmoc strategic synthesis of sulfonopeptides.

Material and Method: Fmoc-protected 2-aminoethanesulfonyl chlorides with different functionalized 1- substituents were synthesized via radical addition of N-Fmoc allylamine and xanthates with functionalized Ssubstituents, and subsequent oxidative chlorination with N-chlorosuccimide/HCl.

Results: Fmoc-protected 2-aminoethanesulfonyl chlorides with different functionalized 1-substituents were synthesized via radical addition and subsequent oxidative chlorination. The mechanism on the oxidative chlorination is proposed.

Conclusion: The current method is an expeditious, convenient, and practical method for the synthesis of Fmocprotected 2-aminoethanesulfonyl chlorides with different functionalized 1-substituents in good to excellent yields.

Keywords: Aminoalkanesulfonyl chloride, radical addition, oxidative chlorination, xanthate, N-chlorosuccimide, Fmoc.

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