Sodium Hydroxide → 3-(4-(3-Methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acid

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Reaction Steps

A solution of methyl 3-(4-(3-methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 45, 0.091 g, 0.290 mmol) and sodium hydroxide (0.50 mL, 1.0 M in water, 0.50 mmol) in methanol (5.0 mL) was stirred for 6 h at room temperature. After this time, the reaction mixture was quenched with 1.0 M hydrochloric acid (0.60 mL), diluted with ethyl acetate and separated. The organic layer was washed with water, and saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, methylene chloride/methanol 49:1) to provide 3-(4-(3-methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoic acid (0.068 g, 75%) as a white solid.

Provenance & Evidence