Hydrochloric Acid → 2-Phenylacetylamino-3,3-bis(4-fluorophenyl)propanoic acid

Participants

Reaction Steps

An aqueous solution (188 mL) of 2-amino-3,3-bis(4-fluorophenyl)propanoic acid hydrochloride (21.50 g, 68.9 mmol) was adjusted to pH 12.2 with 1M aqueous sodium hydroxide solution (154.2 g). Phenylacetyl chloride (10.8 mL, 81.7 mmol) was added dropwise at 0-10° C. while adjusting the mixture to pH 11-12 with 1M aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 3 hrs. Ethyl acetate (400 mL) was added to the reaction mixture, and the mixture was adjusted to pH 1.1 with concentrated hydrochloric acid and partitioned. The obtained organic layer was warmed to 40° C. and hexane (525 mL) was added. The mixture was cooled in an ice bath to allow solid precipitation. The solid was collected by filtration and dried to give the title compound (21.75 g).

Provenance & Evidence