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

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

Volume: 15 Issue: 2

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

Affiliation:

• State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029,China

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

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.

Cite this article as:

Haiouani Kheira , Chen Xingpeng and Xu Jiaxi*, Expeditious Preparation of N-Fmoc 2-Aminoethanesulfonyl Chlorides with Functionalized 1-Substituents, Current Organic Synthesis 2018; 15 (2) . https://dx.doi.org/10.2174/1570179414666170821120705