Hydrochloric Acid → HCID 67331281, compound

Participants

Reaction Steps

To a solution of the oxazolidinone (49.2) (23.0 mg, 0.038 mmol) dissolved in THF (2 mL), was added a 30% hydrogen peroxide solution (43 μL, 0.38 mmol) followed by a 2 M lithium hydroxide solution (94 μL, 0.19 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 49 (5.5 mg). MS ESI (pos.) m/e: 450.1 (M+H). 1H NMR (400 MHz, CD3CN) δ ppm 8.33 (1 H, d, J=1.6 Hz), 7.51 (2 H, d, J=8.6 Hz), 7.12 (2 H, d), 6.95 (2 H, d, J=8.6 Hz), 6.78 (2 H, d, J=8.6 Hz), 6.16 (1 H, d, J=1.6 Hz), 4.44 (1 H, t, J=7.8 Hz), 4.02 (2 H, t, J=6.1 Hz), 3.94 (2 H, t, J=6.1 Hz), 3.09 (1 H, dd, J=16.6, 8.4 Hz), 2.84 (1 H, dd, J=16.4, 7.4 Hz), 1.81-1.84 (4 H, m).

Provenance & Evidence