Trifluoroacetic acid → HCID 178522353, compound

Participants

Reaction Steps

To a solution of 6a (50 mg, 0.16 mmol) in anhydrous dichloromethane (2 was slowly added trifluoroacetic acid (0.5 mL) at room temperature. After overnight stirring, LC-MS indicated 27% starting material remained. Additional trifluoroacetic acid (0.5 mL) was added and the reaction mixture was stirred an additional 24 hours, at which time it was judged complete. The solution was cooled in an ice bath and diluted with additional dichloromethane (10 mL) before the slow addition of saturated sodium bicarbonate solution until the stirring mixture was alkaline. The mixture was then partitioned and the organic solvents were removed and rinsed with brine. The aqueous layer was extracted twice with ethyl acetate and the organic layer was washed with brine. All organics were pooled and dried over anhydrous magnesium sulfate before filtration and solvent evaporation, giving 7a as a light-yellow solid (30 mg, 71%). LC-MS indicated 80% purity, and the material was used in the next step without further purification.

Provenance & Evidence