γ-FLUOROGLUTAMIC ACID
- 1 August 1962
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 40 (8) , 1571-1575
- https://doi.org/10.1139/v62-237
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.Keywords
This publication has 8 references indexed in Scilit:
- Organic compounds of fluorine. II. Fluorinated amino acidsCollection of Czechoslovak Chemical Communications, 1961
- The synthesis of γ-fluoroglutamic acidTetrahedron Letters, 1960
- Proton N.S.R. Spectroscopy. V. Studies of Amino Acids and Peptides in Trifluoroacetic AcidJournal of the American Chemical Society, 1959
- α‐Acylaminoacrylester aus AcylaminomalonesternEuropean Journal of Inorganic Chemistry, 1958
- Toxic Fluorine Compounds. IX.1 ι-Fluorocarboxylic Esters and AcidsThe Journal of Organic Chemistry, 1956
- Ionization Constants of Fluorinated Acids. III. Unsaturated AcidsJournal of the American Chemical Society, 1954
- Synthetic Amino Acids. Syntheses from Acetamidomalonic Ester1Journal of the American Chemical Society, 1945
- CLXXV.—Syntheses with the aid of monochloromethyl ether. Part I. The action of monochloromethyl ether on the sodium derivatives of ethyl malonate and ethyl isopropylmalonateJournal of the Chemical Society, Transactions, 1908