Benzaldehyde → L-Phenylalanine, N-(phenylmethyl)-

Participants

Reaction Steps

The procedure of the process of P. Quitt et al. (Helv. Chim. Acta, 46, 327 (1963)) was followed. A 16.5 g quantity (0.1 mole) of Phe was dissolved in 50 ml of 2N aqueous NaOH solution, 10.1 ml of benzaldehyde was added to the solution with ice-cooling, and the mixture was stirred for about 10 minutes to obtain a uniform reaction mixture. To the mixture was added 1.14 g of NaBH4 in small portions at a temperature of up to 15° C., and the mixture was stirred for 30 minutes. The above procedure was repeated 3 times with use of benzaldehyde and NaBH4, each in one-half the above amount. The reaction mixture was stirred for 2 hours and then washed with ether. The aqueous layer was neutralized with 1N HCl with ice-cooling, and the resulting precipitate was filtered off and dried. The product was recrystallized from a mixture of 50 ml of dimethylformamide (DMF) and 200 ml of methanol to obtain 20.73 g of Nα -benzyl-phenylalanine (BzPhe), yeild 81.2%. M.p. 250°-253° C.

Provenance & Evidence