Water → HCID 59750944, compound

Participants

Reaction Steps

In tetrahydrofuran (4 ml) was dissolved ethyl N-[3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propyl]carbamate (100 mg, 0.239 mmol), followed by the addition of sodium hydride (60% dispersion in mineral oil, 11.5 mg, 0.287 mmol). The resulting mixture was stirred at room temperature for 3 hours. Iodomethane (17.8 μl, 0.287 mmol) was added and the mixture was stirred at room temperature for 15 hours. Sodium hydride (60% dispersion in mineral oil, 5.00 mg, 0.125 mmol) and iodomethane (10.0 μl, 0.161 mmol) were added, followed by stirring at room temperature for 24 hours. Water (5 ml) was added, and the mixture was concentrated. The residue thus obtained was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and then concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated, whereby the title compound (83.2 mg, 0.193 mmol, 81%) was obtained as a colorless oil.

Provenance & Evidence