Tetrahydrofuran → HCID 58459215, compound

Participants

Reaction Steps

To a mixture of tert-butyl 1-(5-fluoro-1-(3-(methylthio)phenyl)-1H-benzo[d]-imidazol-2-yl)ethylcarbamate (0.7397 g, 1.842 mmol) in THF (13.82 mL) and water (4.61 mL) was added oxone (2.83 g, 4.61 mmol) and the mixture was stirred at rt. After 3 h, water (50 mL) was added to the mixture, and extracted with DCM (50 mL×2). The combined organic layers were dried over Na2SO4, filtered, concentrated under reduced pressure to give a white solid, which was purified by column chromatography on a 24 g of Redi-Sep™ Gold column using 0 to 50% gradient of EtOAc in hexane over 5 min and then 50% isocratic of EtOAC for 20 min as eluent to give tert-butyl 1-(5-fluoro-1-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-2-yl)ethylcarbamate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.05-8.15 (2H, m), 7.90 (2H, d, J=4.9 Hz), 7.56 (1H, dd, J=9.5, 2.2 Hz), 7.35 (1H, d, J=8.0 Hz), 7.06-7.18 (2H, m), 4.82-4.95 (1H, m), 3.33 (3H, s), 1.44 (3H, d, J=6.8 Hz), 1.23 (9H, s); LC-MS (ESI) m/z 434.0 [M+H]+.

Provenance & Evidence