1,2-Dichloroethane → HCID 86679548, compound

Participants

Reaction Steps

To a solution of 2-(4-methoxy-3-(methylsulfonyloxy)benzoylthio)acetic acid (0.150 g, 0.468 mmol) in dry DCM (12 ml), EDC (0.090 g, 0.468 mmol) and DMAP (0.057 g, 0.468 mmol) were added followed by (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (0.197 g, 0.468 mmol) and the reaction was stirred at RT for 48 hours. The mixture was partitioned between DCM and HCl 1N; the organic phase was washed with NaHCO3 sat. sol., and dried over Na2SO4. The solvent was removed and the crude was purified by preparative HPLC to afford (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(4-methoxy-3-(methylsulfonyloxy)benzoylthio)-acetoxy)ethyl)pyridine 1-oxide (0.080 g, 0.111 mmol, 23.64% yield, MS/ESI+ 722.38 [MH]+, [αD]=−34.72, c=0.5, DCM).

Provenance & Evidence