L-Phenylalanine → 2-[(2-naphthylsulfonyl)amino]-3-phenylpropanoic acid

Participants

Reaction Steps

A solution of 7.6 mmol (1.71 g) of 2-naphthylsulphonyl chloride in 10 ml of dichloro-methane and a solution of 7.9 mmol (0.32 g) of sodium hydroxide in 10 ml of water are added slowly in succession to 7.6 mmol (1.25 g) of phenylalanine and 7.6 mmol (0.3 g) of sodium hydroxide in 10 ml of water. The reaction mixture is stirred for 1 hour at room temperature. After decanting, the aqueous phase is washed with dichloromethane and rendered acidic to pH=2 with a dilute hydrochloric acid solution. After extraction with dichloromethane, the organic phase is dried over sodium sulphate and concentrated to yield the expected product.

Provenance & Evidence