Chloroacetyl chloride → HCID 66975041, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1RS,2SR)-3-(benzylamino)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-(3-chloro-4-fluorophenyl)propan-1-ol (14.1 g) and triethylamine (4.95 mL) in THF (100 mL) was added chloroacetyl chloride (2.59 ml) under ice-cooling, and the mixture was stirred at 0° C. for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained mixture was diluted with THF (300 ml), 1 N aqueous sodium hydroxide solution (63 mL) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with distilled water, saturated aqueous sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (6.72 g).

Provenance & Evidence