Hydrochloric Acid → HCID 54560925, compound

Participants

Reaction Steps

Acetic anhydride (3 drops) was added to a stirred solution of compound 63 (75 mg, 0.195 mmol), sodium nitrate (17 mg, 0.205 mmol), water (0.3 ml), concentrated HCl (0.16 ml), dichloromethane (0.5 ml), and ether (3 ml). The reaction mixture was stirred for 15 minutes and then more HCl and Ac2O were added until the solution changed color to a bright yellow. After the color had changed, the reaction mixture was stirred for an additional three hours, and then the organic layer was separated, washed with brine, and dried over MgSO4. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-80/20 (Hex/EtOAc). Evaporation of solvent yielded 36 mg (43%) of a yellow solid.

Provenance & Evidence