Amidation of α-Amino Acids Using Dichloro(methyl)(3,3,3-trifluoropropyl)silane and Imidazole without Conventional Protection and Deprotection of α-Amino Group

Tomoya Nobuta*, Honoka Morishita, Yutaka Suto, Noriyuki Yamagiwa

*Faculty of Pharmacy, Takasaki University of Health and Welfare, 60 Nakaorui Takasaki, Gumma, 370-0033, Japan, Email: nobutatakasaki-u.ac.jp

T. Nobuta, H. Morishita, Y. Suto, N. Yamagiwa, Synlett, 2022, 33, 1563-1569.

DOI: 10.1055/a-1865-1792

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Abstract

The combination of dichloro(methyl)(3,3,3-trifluoropropyl)silane (MTFPSCl₂) and imidazole mediates an amidation of amino acids. MTFPSCl₂ activates the carboxy group and protects the α-amino group of amino acids. The corresponding amino acid amides were synthesized in good yields without racemization.

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proposed reactive intermediate

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Key Words

amidation, unprotected amino acid, coupling reagent, silyl reagent, dichloro(methyl)(3,3,3-trifluoropropyl)silane

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ID: J72-Y2022