2-フェニル-5-オキサゾロンとハロゲン化ベンジルとの反応 : α, α-ジ置換アミノ酸の合成および反応に関する研究 (第1報)

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The reaction of benzyl halides with 2-phenyl-5-oxazolone obtained by the dehydration of hippuric acid was carried out in dimethylformamide by use of 50% aqueous solution of potassium hydroxide as a base. After hydrolysis of the reaction mixture, N-benzoyl-α-benzylphenylalanine (1) and its benzyl ester (2) were obtained, respectively, in about 40% and 10% yields. Even when equimolecular amounts of both reactants were used, di substituted derivative (1) was a main product, and monosubstituted derivative (N-benzoyl-dl-phenylalanine) was not obtained, but it was obtained as a by-product by use of quaternary ammonium hydroxide as a base. Disubstituted derivative was obtained in good yield (65% or 59%) by the reaction of benzyl halide derivative having electron-withdrawing group such as p-nitrobenzyl bromide or p-cyanobenzyl bromide.
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