L-Phenylalanine → HCID 272826, compound

Participants

Reaction Steps

A solution of 6.6 mmol (1.0 g) of phenoxyacetic acid in 15 ml of dioxane is treated with 49.3 mmol (3.6 ml) of thionyl chloride. The reaction mixture is stirred at room temperature for 2 hours and then concentrated. The residue, taken up in 10 ml of dichloromethane, and 7.9 mmol (0.3 g) of sodium hydroxide in 10 ml of water are added in succession to a solution of 7.6 mmol (1.25 g) of phenylalanine and 7.6 mmol (0.3 g) of sodium hydroxide in 10 ml of water, the temperature being maintained at 10° C. The reaction mixture is then stirred for 1 hour at room temperature. After decanting, the aqueous phase is washed with dichloromethane, and then rendered acidic to pH=2 with a dilute hydrochloric acid solution. The precipitate that forms is filtered off and recrystallised from water to yield the expected product.

Provenance & Evidence