Ethylamine → HCID 59625404, compound

Participants

Reaction Steps

To a solution of tert-butyl (3R,5S)-3-amino-5-{[(2-tert-butyl-4-{[3-(methylsulfanyl)propyl]amino}pyrimidin-5-yl)carbonyl](2-methylpropyl)amino}piperidine-1-carboxylate (97 mg) and N,N-dimethylpyridin-4-amine (33 mg) in 1,2-dichloroethane (4 ml) was added a solution of 4-nitrophenyl chlorocarbonate (55 mg) in 1,2-dichloroethane (1 ml) under ice-cooling and the mixture was stirred at room temperature for 1 hr. Ethylamine (2 M solution in THF, 450 μl) was added, and the reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object compound (95.9 mg).

Provenance & Evidence