HCID 86679476, compound → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)-2-(3-hydroxy propanoyloxy)ethyl)pyridine 1-oxide

Participants

Reaction Steps

To a mixture of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3-(trityloxy)propanoyloxy)ethyl)pyridine 1-oxide (0.600 g, 0.817 mmol) and Amberlyst 15 (4.7 meq/g, 0.050 g) in dry DCM (20 ml), 3 drops of HBr 48% were added at RT. After 1 hour, the reaction mixture was washed with NaHCO3 sat. sol. and with brine. The organic layer was dried over Na2SO4, the solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel column (DCM:MeOH:32% aq. NH4OH=90:10:1) affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)-2-(3-hydroxy propanoyloxy)ethyl)pyridine 1-oxide (0.311 g, 0.632 mmol, 77% yield, MS/ESI+ 492.1 [MH]+).

Provenance & Evidence