Acetonitrile → HCID 86680462, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Example 202B (40 mg, 0.111 mmol) in anhydrous tetrahydrofuran (1 mL) was added a 0.67 M solution of diazomethane in diethyl ether. The yellow solution was cooled to 0° C., and palladium(II) acetate (1 mg, 4.45 μmol) was added resulting in rapid gas evolution. More diazomethane solution (1 mL) was added dropwise, and the mixture was stirred at 0° C. for 30 minutes. The addition of 1 mL diazomethane solution was repeated several more times at 0° C. while monitoring reaction progress by LCMS (C18 silica gel using a 3 minute gradient of 0-100% acetonitrile in water (0.1% trifluoroacetic acid)). The reaction mixture was concentrated in vacuo and purified by column chromatography on silica gel using a solvent gradient of 0-50% ethyl acetate in hexanes. The title compound was obtained as a colorless oil that crystallized on standing (30 mg, 72%).

Provenance & Evidence