Sodium Iodide → Benzyl N,N-dibenzyl-L-phenylalaninate

Participants

Reaction Steps

L-Phenylalanine (50 g), pulverized potassium carbonate (167 34 g), and sodium iodide (22.68 g) were added to N,N-dimethylacetamide (500 ml) while stirring, and water (25 ml) was added thereto. After elevating the temperature to 60° C., benzyl chloride (118.78 g) was dropwise added. After the dropwise addition, the mixture was vigorously stirred at 60°-65° C. for 6 hours. After the reaction, the reaction mixture was cooled to 20°-30° C., and water (750 ml) and ethyl acetate (500 ml) were added thereto for extraction. The ethyl acetate layer was separated, washed with water (500 ml), an aqueous solution of 10% sodium hydrogensulfite (500 ml×2), and water (500 ml), and concentrated to dryness under reduced pressure to give N,N-dibenzyl-L-phenylalanine benzyl ester (136.88 g) as a yellow, oily substance.

Provenance & Evidence