(S)-3-Phenyl-2-[(pyrazin-2-ylcarbonyl)amino] propanoic acid

73058-37-4

114457-94-2

General procedure for the synthesis of (S)-3-phenyl-2-(pyrazine-2-carboxamido)propionic acid from (pyrazine-2-carbonyl)-L-phenylalanine methyl ester: N-pyrazinecarbonyl-L-phenylalanine methyl ester (1.0 g, 3.51 mmol) was dissolved in 10 mL of acetone, and the pH was adjusted to 12-13 by slowly adding 2N NaOH solution dropwise under cooling in an ice-water bath.Reaction. The progress of the reaction was monitored by thin-layer chromatography (TLC) during the process, and the reaction was completed after 2 hours. Subsequently, hydrochloric acid was slowly added dropwise in an ice-water bath and the pH was adjusted to 2~3, at which time a large amount of white solid precipitated. The precipitate was collected by filtration, washed with water and ether sequentially, and then dried in air. Finally, 0.89 g of white solid product was obtained with a yield of 93.6% and a melting point of 166-169°C. The product structure was analyzed by 1H-NMR. The structure of the product was confirmed by 1H-NMR (DMSO-d6, 300 MHz): δ 3.23 (-CH2, m, 2H), 4.74 (-CH, m, 1H), 7.16-7.25 (-Ph, m, 5H), 8.74 (-CONH, t, 1H), 8.86-8.89 (-Pyz, t, 2H), 9.14 (-Pyz. d, 1H), 13.06 (-COOH, s, 1H).