Hydrochloric Acid → (S)-3-(4-(3-Pivalamidobenzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid

Participants

Reaction Steps

To a solution of the oxazolidinone 30.1 (62.0 mg, 0.107 mmol) dissolved in THF (10 mL), was added a 30% hydrogen peroxide solution (0.120 mL, 1.07 mmol) followed by a 2M LiOH solution (0.266 mL, 0.533 mmol). The resulting slurry was stirred for five 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) and 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 30 (29.0 mg). MS ESI (pos.) m/e: 423.1 (M+H). 1H NMR (400 MHz, CD3CN) δ ppm 8.32 (1 H, d, J=1.6 Hz), 7.92 (1 H, br. s.), 7.61 (1 H, s), 7.42 (1 H, d, J=7.8 Hz), 7.22 (1 H, t, J=7.8 Hz), 7.12 (2 H, d, J=9.0 Hz), 7.05 (1 H, d, J=7.4 Hz), 6.84 (2 H, d, J=9.0 Hz), 6.15 (1 H, d, J=1.6 Hz), 4.95 (2 H, s), 4.43 (1 H, t, J=7.8 Hz), 3.08 (1 H, dd, J=16.6, 8.4 Hz), 2.83 (1 H, dd, J=16.4, 7.4 Hz), 1.16 (9 H, s).

Provenance & Evidence