Facile Preparation of N-Tosyl-L-Phenylalanine Chloromethyl Ketone

Bing-Lei      Gao; Shu-Tao      Ma; Zhao-Peng      Liu

doi:10.2174/157017809790443005

Abstract

A method for the facile preparation of N-tosyl-L-phenylalanine chloromethyl ketone was developed. LPhenylalanine was tosylated and converted to the activated ester of p-nitrophenol. Subsequent reaction with dimethylsulfoxonium methylide and treatment with lithium chloride and methanesulfonic acid afforded the α- chloroketone. This practical procedure avoided the use of toxic and explosive diazomethane.

Keywords: Serine protease inhibitors, α-chloroketone, N-tosyl-L-phenylalanine chloromethyl ketone, ylides, sulfur

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Letters in Organic Chemistry

Title: Facile Preparation of N-Tosyl-L-Phenylalanine Chloromethyl Ketone

Volume: 6 Issue: 8

Author(s): Bing-Lei Gao, Shu-Tao Ma and Zhao-Peng Liu

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Keywords: Serine protease inhibitors, α-chloroketone, N-tosyl-L-phenylalanine chloromethyl ketone, ylides, sulfur

Abstract: A method for the facile preparation of N-tosyl-L-phenylalanine chloromethyl ketone was developed. LPhenylalanine was tosylated and converted to the activated ester of p-nitrophenol. Subsequent reaction with dimethylsulfoxonium methylide and treatment with lithium chloride and methanesulfonic acid afforded the α- chloroketone. This practical procedure avoided the use of toxic and explosive diazomethane.

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Gao Bing-Lei, Ma Shu-Tao and Liu Zhao-Peng, Facile Preparation of N-Tosyl-L-Phenylalanine Chloromethyl Ketone, Letters in Organic Chemistry 2009; 6 (8) . https://dx.doi.org/10.2174/157017809790443005