Methyl 2-(benzylamino)-2-phenylacetate → (Benzylamino)Phenylacetic Acid

Participants

Reaction Steps

A solution of methyl 2-(benzylamino)-2-phenylacetate (1.00 g, 3.90 mmol) in THF (90 ml) and 1N NaOH (10 ml) was stirred at room temperature overnight (LC-MS monitoring: complete conversion). The solvent was removed under reduced pressure, and the crude product was partitioned between EtOAc and water. The aqueous phase was acidified with conc. HCl (pH about 3) and then extracted with EtOAc (three times). The organic phase was dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (940 mg, quantitative yield), which is used in the next step without any further purification.

Provenance & Evidence