Author:
Buchanan R. L.,Dean F. H.,Pattison F. L. M.
Abstract
The synthesis of γ-fluoroglutamic acid, HOOCCHFCH2CH(NH2)COOH, was achieved by two independent methods, both of which involved the Michael reaction: (1) methyl α-fluoroacrylate and diethyl acetamidomalonate gave the transesterified intermediate, which on hydrolysis produced γ-fluoroglutamic acid (31% yield); (2) ethyl α-acetamidoacrylate and diethyl fluoromalonate reacted under mild conditions to give, after hydrolysis, the required amino acid in 56% overall yield. Of the two procedures, the second is preferable, since it is based on more readily available starting materials and gives a higher yield.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
40 articles.
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1. Ethyl 2-acetamido Acrylate;Encyclopedia of Reagents for Organic Synthesis;2014-05-27
2. Flourishing Frontiers in Organofluorine Chemistry;Organic Chemistry - Breakthroughs and Perspectives;2012-08-23
3. Vitamin-K-dependent carboxylation;International Journal of Peptide and Protein Research;2009-01-12
4. A convenient transformation of α-alkylserines into α-halogenomethyl-α-alkylglycines;Tetrahedron Letters;2008-11
5. Diethyl Fluoromalonate;Encyclopedia of Reagents for Organic Synthesis;2006-09-15