Hydrochloric Acid → HCID 10053779, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve the compound of Example 19 (250 mg, 0.42 mmol) in dichloromethane (5 mL). Add 2M HCl in ether (0.42 mL, 0.84 mmol) and stir for 1 minute. Remove the solvent in vacuo and place on a high vacuum pump for 10 minutes. Dissolve the foam in dry dichloromethane (5 mL), cool to 0° C. and add BBr3 (0.20 mL, 2.1 mmol), dropwise. After 25 minutes, slowly pour into saturated aqueous sodium bicarbonate (10 mL) and extract with dichloromethane (2×10 mL). Dry the combined organic layers with sodium sulfate and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting with methanol (3 to 5%) in dichloromethane with 0.2% ammonium hydroxide to yield 196 mg of the title compound (81%): mass spectrum (ion spray) m/z=572.3 (M+H).

Provenance & Evidence