Hydrochloric Acid → (S)-3-(Isoxazol-3-yl)-3-(4-(2-(4-(trifluoromethyl)phenoxy)propoxy)phenyl)propanoic acid

To a solution of the oxazolidinone (48.2) (39.0 mg, 0.066 mmol) dissolved in THF (3 mL), was added a 30% hydrogen peroxide solution (74 μL, 0.66 mmol) followed by a 2 M lithium hydroxide solution (160 μL, 0.33 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 48 (7.5 mg). MS ESI (pos.) m/e: 436.1 (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, J=9.0 Hz), 6.97 (2 H, d, J=8.6 Hz), 6.80 (2 H, d), 6.14 (1 H, d, J=1.6 Hz), 4.43 (1 H, t, J=7.8 Hz), 4.12 (2 H, t, J=6.3 Hz), 4.05 (2 H, t, J=6.3 Hz), 3.08 (1 H, dd, J=16.4, 8.2 Hz), 2.83 (1 H, dd, J=16.6, 7.2 Hz), 2.06-2.19 (2 H, m).

1. extractionThe mixture was then extracted with EtOAc (1×20 mL)
2. washthe organic layer was washed with an acidic sodium sulfite solution (2×15 mL) and brine (1×15 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-6740d8ef2d764522bffb9b0341e409e5

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003648B2