1,4-Dioxane → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3-(3-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoyloxy)propanoyloxy)ethyl)-pyridine 1-oxide

Participants

Reaction Steps

To a solution of (S)-4-(2-(3-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoyloxy)propanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.450 g, 0.523 mmol) in dry DCM (15 ml), 4M HCl in dioxane (0.654 ml, 2.62 mmol) was added. The resulting mixture was stirred at RT for 4 days. The solvent was evaporated and the residue was purified by trituration with Et2O (30 ml) affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3-(3-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoyloxy)propanoyloxy)ethyl)-pyridine 1-oxide (0.340 g, 0.448 mmol, 86% yield, MS/ESI+759.31 [MH]+, [αD]=−8.9, c=0.6, DCM).

Provenance & Evidence