Sodium Hydroxide → 3-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]propanoic acid

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Reaction Steps

1N NaOH (5 mL) was added to an ice-cooled solution of crude ethyl 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoate (450 mg, 1.61 mmol) in MeOH (5 mL) and the solution was allowed to stir at room temperature for 1 h. Solvent was evaporated and the reaction mixture was diluted with water. The aqueous layer was washed with EtOAc and the pH of the aqueous solution was adjusted to ˜2 using 1N HCl. The organic product was extracted with EtOAc and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 3-(4-(4-fluorophenyl)thiazol-2-yl)propanoic acid (320 mg, yield 79%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 12.29 (br s, 1H), 7.99-7.96 (m, 2H), 7.93 (s, 1H), 7.28-7.22 (t, J=9.0 Hz, 2H), 3.25-3.20 (t, J=7.1 Hz, 2H), 2.78-2.74 (t, J=7.1 Hz, 2H). MS (ESI) m/z: Calculated for C12H10FNO2S: 251.04. found: 252.2 (M+H)+.

Provenance & Evidence