Sodium Hydroxide → (R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid

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Reaction Steps

To a stirred solution of title D compound, (R)-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester (0.47 g, 0.99 mmol) in methanol (25 mL) is added sodium hydroxide (0.16 g, 3.95 mmol) in water (5 mL) at RT. The reaction mixture is stirred for 16 h. The reaction mixture is concentrated at reduced pressure, poured into water, the aqueous layer is separated, washed with ethyl acetate twice, acidified with concentrated HCl and extracted three times with ethyl acetate. The combined ethyl acetate extract is dried and concentrated to give (R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid as a white solid: MS m/z 447.3 [M−1]−.

Provenance & Evidence