tert-Butanol → HCID 21099527, compound

Participants

Reaction Steps

To dichloromethane (1 mL) at 0° C. was added chlorosulfonyl isocyanate (0.03 mL, 0.26 mmol) and tert-butanol (0.03 mL, 0.26 mmol). The mixture was stirred for 10 minutes then triethylamine (0.054 mL, 0.39 mmol) was added followed by [3-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]amine hydrochloride (Example 212, 100 mg, 0.26 mmol). The reaction was allowed to warm to room temperature and stirred for 2 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was treated with trifluoroacetic acid for 15 minutes then evaporated. The residue was partitioned between ethyl acetate and 1M sodium hydroxide. The organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography on silica, eluting with 50% ethyl acetate/isohexane to give the title compound (40 mg, 36%). δH (500 MHz, d6 DMSO): 9.94 (1H, s), 7.89 (2H, d, J=8.4 Hz), 7.79 (2H, d, J=8.4 Hz), 7.71-7.65 (3H, m), 7.51-7.48 (2H, m), 7.44-7.38 (2H, m), 7.30-7.20 (5H, m); m/z (ES+) 431 [MH+].

Provenance & Evidence