Ethyl 2-benzoylglycinate

An anhydride [2309, 2323] (catalysed by mineral acid) or ethyl hippurate (ethyl 2-benzoylglycinate) [2186] cyclizes an o-aminophenol on prolonged refluxing. Chloral hydrate and hydroxylamine convert an aminophenol into a benzoxazole-2-carboxaldehyde oxime [2104]. 

In order to obtain basic information with regard to amino acid incorporation, Aso et al. (62) investigated a model system in which ethyl hippurate (i.e., N-benzoylglycine ethyl ester) was used as substrate instead of a protein hydrolysate. Ethyl hippurate (50mM) was first incubated with papain (1.7 X 10"2mM) at pH 6.0 and 37°C. After 15... 

Unsaturated a-Amino-acids. - Oxazolinones (515), readily derived from N-benzoylglycine and ethyl chloroformate, condense smoothly with aromatic aldehydes, N-phenylaldimines, or cyclohexanone to... 

Years later, it was found that the reaction of ethyl formate with the ethyl ester of hippuric acid (ethyl A-benzoylglycine) in the presence of sodium ethoxide would lead to an aldol adduct, the reduction and hydrolysis of which generates racemic serine (Ser, S) (Scheme 12.40). 

Gyanomethyl N-benzoylglycinate refluxed 20-40 hrs. with 1.2 moles of p-nitro-phenylhydrazine in ethyl acetate -> hippuric acid p-nitrophenylhydrazide. Y 90%.—Similar reactions with the analogous methyl esters failed. F. e. s. P. Grud-zinska, Roczniki Ghem. 34, 1687 (1960). 

A soln. of ethyl a-benzoylglycinate hydrochloride in HCl-methanol-water stirred and electrolyzed at an initial voltage of 10 v. and a current density of 0.03 amp./ cm2 in a cathodic compartment with a Hg-pool electrode, separated by a pottery membrane from the anodic compartment, whidi contains a Pt-electrode, aq. 50%-methanol, and some HCl ethyl benzoylacetate. Y 90%. F. e. s. K. Matsumoto et al., J. Org. Chem. 38, 2731 (1973). 

---