反应详情

温度

60 °C

To a solution of crude tert-butyl {(3S,5S)-5-(2,3-difluorophenyl)-2-[(4,4,4-trifluoro-2-hydroxybutyl)imino]piperidin-3-yl}carbamate (99.0 mg, 0.219 mmol) in acetonitrile (2.19 mL) was added pyridinium dichromate (247 mg, 0.657 mmol), and the mixture was stirred 2.5 h at 60° C. Pyridinium dichromate (392 mg, 1.04 mmol) was added and the resulting mixture stirred 72 h at 60° C. Pyridinium dichromate (300 mg, 0.797 mmol) was added and the resulting mixture stirred 4 h at 60° C. The mixture was cooled to ambient temperature and saturated aqueous sodium bicarbonate was added. Water was added, and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase chromatography (C-18, 95% water/acetonitrile→15% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (59 mg). MS 432.2 (M+1).

1. stirringthe resulting mixture stirred 72 h at 60° C
2. stirringthe resulting mixture stirred 4 h at 60° C
3. temperatureThe mixture was cooled to ambient temperature
4. extractionthe mixture was extracted with ethyl acetate (3×)
5. washThe combined organic extracts were washed with brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by reverse phase chromatography (C-18, 95% water/acetonitrile→15% water/acetonitrile with 0.1% trifluoroacetic acid)