Water → 3-(4-(3-Cyano-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acid

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Reaction Steps

A solution of methyl 3-(4-(3-cyano-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 46, 0.276 g, 0.851 mmol), lithium hydroxide (0.024 g, 1.00 mmol) and water (0.016 g, 0.889 mmol) was stirred at 0° C. for 4 h and then warmed to room temperature overnight. After this time, the reaction mixture was quenched with 1.0 M hydrochloric acid (1.0 mL), diluted with ethyl acetate and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by preparative HPLC (95% water-acetonitrile with 0.05% v/v trifluoroacetic acid/95% acetonitrile-water with 0.05% v/v trifluoroacetic acid 1:1, 15 mL/min) to provide 3-(4-(3-cyano-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acid (0.035 g, 13%) as a white solid.

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