Cesium carbonate → (S)-4-Benzyl-3-((S)-3-(isoxazol-3-yl)-3-(4-(2-(4-(trifluoromethyl)phenoxy)propoxy)phenyl)propanoyl)oxazolidin-2-one

The bromide 48.1 (80 mg, 0.16 mmol) was dissolved in DMF (2.0 mL). Cesium carbonate (200 mg, 0.62 mmol) and 4-trifluoromethylphenol (100 mg, 0.62 mmol) were added to the solution and the mixture was then heated with stirring for three hours. The reaction mixture was then cooled to room temperature and diluted with water. The mixture was extracted with EtOAc (2×50 mL). The combined organic layers were washed with 1M lithium chloride solution (1×25 mL), water (1×25 mL) and brine (1×25 mL) and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue purified by medium pressure chromatography (silica, 0 to 60% EtOAc: hexanes) to obtain 48.2 (39 mg). MS ESI (pos.): m/e 595.2 (M+H).

1. temperaturethe mixture was then heated
2. extractionThe mixture was extracted with EtOAc (2×50 mL)
3. washThe combined organic layers were washed with 1M lithium chloride solution (1×25 mL), water (1×25 mL) and brine (1×25 mL)
4. dry with materialdried over magnesium sulfate
5. concentrationThe filtrate was concentrated under reduced pressure
6. customthe residue purified by medium pressure chromatography (silica, 0 to 60% EtOAc: hexanes)

ORD record

ord-e837a19a38c84ad18df39b8e25a35922

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003648B2