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

Participants

Reaction Steps

To a solution of crude (S)-4-(2-(2-(2-(3-(N-(tert-butoxycarbonyl)-methylsulfonamido)-4-(cyclopropylmethoxy)phenyl)acetoxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (theoric 0.501 mmol) in DCM (5 ml), HCl 4M in dioxane (1.309 ml, 5.23 mmol) was added and the mixture was reacted for 4 hours at RT. The solvents were evaporated to dryness, and the resulting crude was purified by preparative LC-MS recovering the desired product (102.5 mg, 0.135 mmol, 26.9% yield over two steps, MS/ESI+ 759.46 [MH]+, [αD]=+47.84, c=0.25, DCM).

Provenance & Evidence