Hydrochloric Acid → HCID 24898551, compound

To a solution of the oxazolidinone (33.1) (106 mg, 0.154 mmol) dissolved in THF (7 mL), was added a 30% hydrogen peroxide solution (175 μL, 1.54 mmol) followed by a 2 M LiOH solution (383 μL, 0.765 mmol). The resulting slurry was stirred for five hours. The reaction mixture was diluted with water and acidified with hydrochloric acid to pH ˜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 33 (52.0 mg). MS ESI (pos.) m/e: 532.0 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.22 (1 H, d, J=1.6 Hz), 8.00 (2 H, d, J=8.2 Hz), 7.94 (1 H, s), 7.83 (1 H, d, J=7.8 Hz), 7.70 (2 H, d, J=8.6 Hz), 7.59 (1 H, d, J=7.8 Hz), 7.48 (1 H, t, J=7.6 Hz), 7.12 (2 H, d, J=9.0 Hz), 6.82 (2 H, d, J=8.6 Hz), 6.00 (1 H, d, J=1.6 Hz), 5.00 (2 H, s), 4.48 (1 H, t, J=7.6 Hz), 3.27 (1 H, dd, J=16.8, 7.8 Hz), 2.90 (1 H, dd, J=16.6, 7.6 Hz).

1. extractionThe mixture was then extracted with EtOAc (3×30 mL)
2. washthe organic layer was washed with an acidic sodium sulfite solution (1×30 mL) and brine (1×30 mL)
3. dry with materialdried over magnesium sulfate
4. concentrationThe filtrate was concentrated under reduced pressure
5. customthe residue was purified by reverse phase HPLC

ORD record

ord-0fff7708be464acf9073afe406000d6a

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003648B2