1,4-Dioxane → HCID 71542651, compound

Participants

Reaction Steps

To a solution of (S)-4-(2-(2-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoyloxy)-2-methylpropanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (168 mg, 0.192 mmol) in dry DCM (2 ml), HCl 4M in dioxane (144 μl, 0.577 mmol) was added with stirring at RT for 2 days. Additional HCl 4M in dioxane (144 μl, 0.577 mmol) was freshly added and the stirring was continued for further 3 days. The volatiles were removed under vacuum, and the crude was purified by preparative HPLC. After evaporation of the solvent, the residue was triturated with iPr2O and collected by filtration to give (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(3-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoyloxy)-2-methylpropanoyloxy)ethyl)pyridine 1-oxide as a white solid (50 mg, 0.065 mmol, 33.6% yield, MS/ESI+ 773.29 [MH]+, [αD]=−18.13, c=0.60, MeOH).

Provenance & Evidence