Sodium Hydroxide → 4-[(1S)-1-[[(2R)-3-methyl-2-(2-phenoxyethoxy)butanoyl]amino]ethyl]benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-[(1S)-1-[[(2R)-3-methyl-2-(2-phenoxyethoxy)butanoyl]amino]ethyl]benzoate (30 g, 75.1 mmol) in THF (300 mL) is added 2N NaOH (94 mL, 188 mmol). The mixture is stirred at 55° C. overnight, cooled, and concentrated to remove THF. The aqueous residue is diluted with water (200 mL) and extracted with ethyl acetate (2×200 mL). The organic layers are discarded. The aqueous layer is acidified to pH 2 using conc. HCl (25 mL) and extracted with ethyl acetate (2×200 mL). The combined ethyl acetate layers are dried with MgSO4, filtered, and concentrated. The material is slurried with heptane (500 mL) at 60° C. for 2 h, cooled to room temperature, and filtered. The resulting solid is slurried with water (500 mL) at 60° C. for 2 h, cooled to room temperature, filtered, and dried at 40° C. to provide the title compound as a white solid (20 g, 69%). MS (m/z): 386.0 (M+1).

Provenance & Evidence