Potassium Fluoride → (R)-tert-Butyl 3-(3-(2-fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)ureido)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of (R)-tert-butyl 3-(3-(4-(4-(4-(2-(tert-butyldimethylsilyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)benzyl)piperazine-1-carbonyl)-2-fluorophenyl)ureido)-pyrrolidine-1-carboxylate (0.372 mmol, 300 mg) in tetrahydrofuran (10 mL) was added potassium fluoride (50% weight on celite) (3.72 mmol, 433 mg). The resulting suspension was heated to 80° C. for 16 hours. The reaction mixture was filtered through celite and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel (eluting with dichloromethane—5% methanol/95% dichloromethane gradient) to afford the title compound (210 mg). MS (ESI) m/z 692.3 [M+H]+

Provenance & Evidence