Hydrochloric Acid → HCID 24898549, compound

Participants

Reaction Steps

To a solution of the oxazolidinone (31.4) (73.0 mg, 0.111 mmol) dissolved in THF (11 mL), was added a 30% hydrogen peroxide solution (125 μL, 1.11 mmol) followed by a 2 M LiOH solution (277 μL, 0.555 mmol). The resulting slurry was stirred for five hours. The reaction mixture was diluted with water and acidified with hydrochloric acid to a pH of 3. The mixture was then extracted with EtOAc (3×30 mL), and the organic layer was washed with an acidic sodium sulfite solution (1×30 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 31 (29.0 mg). MS ESI (pos.) m/e: 500.0 (M+H). 1H NMR (400 MHz, CD3CN) δ 8.32 (1 H, d, J=1.6 Hz), 7.44-7.51 (3 H, m), 7.33-7.41 (3 H, m), 7.24 (2 H, d, J=8.2 Hz), 7.12 (2 H, d, J=8.6 Hz), 6.82 (2 H, d, J=9.0 Hz), 6.15 (1 H, d, J=1.6 Hz), 4.98 (2 H, s), 4.44 (1 H, t, J=7.8 Hz), 3.08 (1 H, dd, J=16.4, 8.2 Hz), 2.83 (1H, dd, J=16.4, 7.4 Hz).

Provenance & Evidence