Γ-Fluoroglutamic ACID

Abstract

The synthesis of r-fluoroglutamic acid, HOOCCIIFCHyCH(.\'I-I2)COOI-I, was achieved by two independent methods, both of which involved the Michael reaction: (1) methyl a-fluoroacrylate and diethyl acetamido~nalonate gave the transesterilied intermediate, which on hydrolysis produced r-lluoroglutamic acid (3lC% yield); (2) ethyl a-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 Inore readily available starting ~naterials and gives a higher yield.

Synthesis, reactions, and applications of fluorine-containing multifunctional carbon compounds

“…Treatment of several a-fluoro ketones or esters 1 having one or two additional fluorine or bromine atoms at the a-position of the carbonyl group, with zinc and trimethylsilyl chloride in acetonitrile gave the corresponding enol silylethers 2 (M = TMS) (Scheme 1) [11]. Although electrophilic nitration of the enol silylethers and the corresponding lithium or sodium enolates 2 (M = Li, Na) [12][13][14] was attempted, under various conditions (PrONO 2 /TBAF [15], O 2 NBF 4 /HF/Pyridine [16], or NH 4 ONO 2 /TFAA [17]), the desired compound 3 could not be obtained. Both electrophilic amination (R 2 NOR 0 ) [18] and sulfenylation (PhSCl, PhSSPh) of them were also unsuccessful.…”

A convenient transformation of α-alkylserines into α-halogenomethyl-α-alkylglycines

“…Only a few synthetic strategies directed toward the synthesis of the selected a-halogenomethylamino acids have been described. [11][12][13][14] obtained various racemic a-halogeno- The starting N-Boc-a-alkylserines 2 were synthesized from the potassium salt of a-alkylserines 1 and Boc 2 O in boiling methanol in the presence of triethylamine as a base. Using these reaction conditions, we were able to obtain products 2 in high yields (79-84%) after 3-4 h. The standard procedure for the synthesis of N-Boc-aalkylserines usually takes two to three days.…”

“…doi:10.1016/j.tetlet.2008.aryl-3-carbobenzyloxy oxazolidinones with ICH 2 X 13. Buchanan et al obtained racemic c-fluoroglutamic acid via two independent methods, both of which involved a Michael reaction 14. Scheme 1 outlines our method for the synthesis of N-protected a-chloromethyl-and a-bromomethyl-a-alkylamino acids.…”

Synthesis of some racemic?-fluoro-?-amino acids

“…In this way a series of monofluorinated aliphatic amino acids has been prepared (Raasch, 1958;Hudlkck~, 1960Hudlkck~, , 1961Tolman et al, 1967Tolman et al, , 1983Tolman et al, , 1993. Alternatively 2-fluoromalonate and ethyl 2-acetamidoacrylate have been used for the Michael-type bond formation (Buchanan et al, 1962). Furthermore, Sch611kopf's (1983) bis-lactimether methodology has been used for the synthsis of ethyl (+)-y-fluoroleucinate (Papageorgiou et al, 1994).…”