Dimethyl Sulfoxide → HCID 69103452, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (2R)-2-[6-(acetylamino)-3-pyridyl]-2-[[tert-butyl(dimethyl)silyl]oxy]ethyl 4-methylbenzenesulfonate (3.50 g), (2-(4-bromophenyl)ethyl]-amine (3.01 g) and dimethyl sulfoxide (1.75 ml) was added N,N-diisopropylethylamine (1.31 ml) and the mixture was stirred at 80° C. for 24 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (35 ml) and water (35 ml), and the organic layer was separated. The organic layer was washed with water (35 ml×2) and brine (35 ml), and dried over magnesium sulfate. Filtration followed by evaporation gave a yellow paste (5.36 g) which was chromatographed on silica gel (eluent: hexane/ethyl acetate) to give N-[5-[(1R)-2-[[2-(4-bromophenyl)ethyl]-amino]-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-2-pyridyl]acetamide (3.33 g) as a colorless paste.

Provenance & Evidence