1,4-Dioxane → HCID 71543017, compound

Participants

Reaction Steps

To a solution of (S)-4-(2-(2-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoylthio)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.046 g, 0.053 mmol) in DCM (2 ml), HCl 4M in dioxane (0.013 ml, 0.053 mmol) was added and the resulting mixture was stirred at RT overnight. Three more additions of HCl 4M in dioxane (0.265 ml, 1.06 mmol) over five days were performed. The volatiles were removed under vacuum and the crude was purified by filtration through a silica gel cartridge (DCM:Et2O=7:3) affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(3-(cyclopropylmethoxy)-4-(methylsulfonamido)-benzoylthio)acetoxy)ethyl)pyridine 1-oxide as a colorless oil (0.032 g, 0.042 mmol, 79% yield, MS/ESI+ 761.26 [MH]+, [αD]=−46.44, c=0.5, MeOH).

Provenance & Evidence