Ammonium Chloride → HCID 178454139, compound

Participants

Reaction Conditions

Reaction Steps

[(3S)-3-[(tert-Butoxycarbonyl)amino]-4-{[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]amino}-4-oxobutyl](dimethyl)sulfonium iodide (919 mg) was dissolved in tetrahydrofuran (9.2 mL), and cooled to 0° C. under a nitrogen air flow, and a 1.6 M solution (0.7 mL) of hexamethyldisilazanelithium in tetrahydrofuran was added dropwise thereto, followed by stirring at 0° C. for 2 hours. A 1.6 M solution (0.7 mL) of hexamethyldisilazanelithium in tetrahydrofuran was further added dropwise thereto, followed by stirring at 0° C. for 1 hour. A saturated aqueous ammonium chloride solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30-0:100) to obtain tert-butyl{(3S)-1-[trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexyl]-2-oxopyrrolidin-3-yl}carbamate (154 mg).

Provenance & Evidence