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

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To a solution of methyl 4-[(1S)-1-[[(2R)-3-methyl-2-(2-phenoxyethoxy)butanoyl]amino]ethyl]benzoate (2.0 g, 5.01 mmol) in MeOH (25 mL) and THF (25 mL) is added 5N NaOH (10 mL, 50 mmol). The mixture is stirred at room temperature for 1.5 h, treated with 5N HCl (10 mL), and concentrated to remove organic solvents. The aqueous residue is extracted with ethyl acetate (3×30 mL). The combined ethyl acetate layers are dried with MgSO4, filtered, and concentrated. The crude material (1.36 g) is dissolved in ethyl acetate and washed with 1N NaOH (25 mL). The aqueous layer is extracted with ethyl acetate (25 mL), acidified with 1N HCl (25 mL), and extracted with ethyl acetate (3×25 mL). The combined ethyl acetate layers are dried with MgSO4, filtered, and concentrated to a waxy solid. This material is co-evaporated with MeOH (3×) to provide the title compound as a white solid (925 mg, 48%). MS (m/z): 386.2 (M+1).

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