Hydrochloric Acid → HCID 24799998, compound

Participants

Reaction Steps

Methyl 6-(2-(3-(4-phenoxyphenyl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate (356 mg, 0.831 mmol) was dissolved in THF/H2O (3:2, 75 mL) and LiOH (59 mg, 2.5 mmol) was added. The reaction solution was stirred at room temperature under an atmosphere of Ar for 2 h before the addition of 1 N HCl to adjust the solution to an acidic pH to quench the reaction. The reaction solution was diluted with EtOAc and the organic and aqueous layers were separated. The aqueous layer was extracted with EtOAc (3×). The organic phases were combined and washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 1% AcOH/EtOAc) to provide 6-(2-(3-(4-phenoxyphenyl)propanoyl)oxazol-5-yl)pyridine-2-carboxylic acid as a light yellow solid (314 mg, 91%): 1H NMR (THF-d8, 500 MHz) δ 8.11-8.03 (m, 4H), 7.30-7.25 (m, 4H), 7.03 (t, 1H, J=8.0 Hz), 6.94 (d, 2H, J=8 Hz), 6.91 (d, 2H, J=8.5 Hz), 3.43 (t, 2H, J=7.5 Hz), 3.04 (t, 2H, J=7.5 Hz); 13C NMR (THF-d8, 500 MHz) δ 187.3, 165.7, 158.9, 156.7, 153.6, 150.1, 147.2, 139.7, 137.1, 130.7, 130.6, 128.7, 125.5, 123.8, 123.7, 120.0, 119.4, 41.7, 29.8; HR ESI-TOF m/z 415.1284 (M+H+, C24H18N2O5, requires 415.1288).

Provenance & Evidence