Hydrochloric Acid → (-)-N-Acetylphenylalanine

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Reaction Steps

To a stirred solution of 20.0 parts of D-phenylalanine in 121 parts of water, cooled to about 1°-2°, is added, portionwise, an aqueous 50% sodium hydroxide solution until pH 12 is reached. Then 37 parts of acetic anhydride is added, while continuously adding aqueous 50% sodium hydroxide to keep the pH at about 12 and cooling the solution to keep the temperature at between about 10° to 30°. After about 20 minutes the mixture is acidified to pH 1 with concentrated hydrochloric acid and filtered. The recovered solid is recrystallized from water to afford N-acetyl-D-phenylalanine, melting at about 170°-172°.

Provenance & Evidence