Hydrochloric Acid → (S)-3-(4-(3-(4-(Trifluoromethyl)benzamido)benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid

Participants

Reaction Steps

To a solution of oxazolidinone 27.4 (71.8 mg, 0.107 mmol) dissolved in THF (10 mL), was added a 30% hydrogen peroxide solution (0.121 mL, 1.07 mmol) followed by a 2M LiOH solution (0.268 mL, 0.535 mmol). The resulting slurry was stirred for two hours. The reaction mixture was diluted with water and acidified with hydrochloric acid to a pH 3. The mixture was then extracted with EtOAc (1×50 mL), and the organic layer was washed with acidic sodium sulfite solution (2×30 mL), brine (1×30 mL), and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure, and the residue was purified by reverse phase HPLC to give 27 (25.2 mg). MS ESI (pos.) m/e 511.1 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.21 (1 H, br. s.), 10.51 (1 H, s), 8.75 (1 H, d, J=1.6 Hz), 8.15 (2 H, d, J=8.2 Hz), 7.91 (2 H, d, J=8.2 Hz), 7.87 (1 H, s), 7.74 (1 H, d, J=8.2 Hz), 7.38 (1 H, t, J=7.8 Hz), 7.23 (2 H, d, J=8.6 Hz), 7.19 (1 H, d, J=7.8 Hz), 6.96 (2 H, d, J=9.0 Hz), 6.50 (1 H, d, J=1.6 Hz), 5.08 (2 H, s), 4.48 (1 H, t, J=7.8 Hz), 3.07 (1 H, dd, J=16.4, 8.2 Hz), 2.88 (1 H, dd, J=16.2, 7.2 Hz).

Provenance & Evidence