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

Participants

Reaction Steps

To a solution of the oxazolidinone (32.1) (17.0 mg, 0.0241 mmol) dissolved in THF (2 mL), was added a 30% hydrogen peroxide solution (27.0 μL, 0.241 mmol) followed by a 2 M LiOH solution (60.0 μL, 0.121 mmol). The resulting slurry was stirred for one hour. The reaction mixture was then diluted with water and acidified with hydrochloric acid to pH ˜3. The mixture was then extracted with EtOAc (1×20 mL), and the organic layer was washed with an acidic sodium sulfite solution (2×15 mL) and brine (1×15 mL), and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure, and the residue was purified by reverse phase HPLC to give 32 (6.00 mg). MS ESI (pos.) m/e: 547.0 (M+H). 1H NMR (400 MHz, CD3CN) δ ppm 8.32 (1H, d, J=1.6 Hz), 7.81 (2H, d, J=8.2 Hz), 7.69 (2H, d, J=8.2 Hz), 7.04-7.23 (5H, m), 6.95 (1H, d, J=7.8 Hz), 6.79 (2H, d, J=9.0 Hz), 6.15 (1H, d, J=1.6 Hz), 4.91 (2H, s), 4.44 (1H, t, J=7.8 Hz), 3.08 (1H, dd, J=16.4, 8.2 Hz), 2.83 (1H, dd, J=16.4, 7.4 Hz).

Provenance & Evidence