Methyl bromoacetate → HCID 86585710, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-hexanoyl-4-(S)-benzyloxazolidin-2-one (7.3 mmol) in THF at −78° C. was added 1.0 M sodium hexamethyldisilazide (NaHMDS, 8.8 mmol) and the reaction stirred at −78° C. for 1 hr. A solution of methyl bromoacetate (8.8 mmol) in THF was then added dropwise, and the resulting mixture was stirred at −78° C. for 1 hr and then at room temperature overnight. The reaction was quenched with NH4Cl, concentrated, then suspended in ethyl acetate and washed with 0.5 N HCl and brine, dried, and purified by silica gel chromatography (ethyl acetate/hexanes) to afford the methyl 3-(R)-(n-butyl)-3-[4-(S)-benzyloxazolidin-2-one-3-ylcarbonyl)propionate.

Provenance & Evidence