Submit Manuscript  

Article Details


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

[ Vol. 15 , Issue. 2 ]

Author(s):

Kheira Haiouani, Xingpeng Chen and Jiaxi Xu*   Pages 246 - 255 ( 10 )

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.

Affiliation:

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

Graphical Abstract:



Read Full-Text article