Dichloromethane methanol → HCID 90041879, compound

Participants

Reaction Steps

Sodium periodate (21.9 mg, 0.102 mmol) was added to a stirred suspension of (3R,3aR,6R,6aS)-3-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-6-vinyl-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-ol (23.4 mg, 0.049 mmol) and ruthenium(III) chloride hydrate (1.0 mg, 4.44 μmol) in acetonitrile (0.42 ml) and water (0.07 ml). The reaction mixture was stirred at room temperature for 4 h, then partitioned between EtOAc (20 ml) and saturated aqueous sodium thiosulfate (20 ml). The aqueous layer was extracted with EtOAc (2×20 ml). The organic layers were combined, washed with brine (1×10 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a colorless residue. The residue was dissolved in EtOAc/MeOH and loaded onto a 500 micron 20 cm×20 cm silica gel plate, which was developed twice using 5% MeOH/DCM. The silica containing the product band was collected and eluted with 10% MeOH/DCM (80 ml). The solvent was evaporated under reduced pressure to give the title compound as a colorless residue. LC-MS: calculated for C25H20ClN3O5 477.11 observed m/e: 478.05 (M+H)+ (Rt 1.15/2 min)

Provenance & Evidence