Pivaloyl chloride → (4S)-4-benzyl-3-(2-isopropoxyacetyl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution containing 98 g of 2-isopropoxyacetic acid and 360 ml of triethylamine in tetrahydrofuran (4L) was cooled to −25° C. After 92 ml of 2,2-dimethylpropanoyl chloride was dropwise added, the reaction solution was stirred at −20° C. for 5 hours. Then, 50 g of anhydrous lithium chloride and 120 g of (4S)-4-benzyl-1,3-oxazolidin-2-one were successively added, and stirring was continued at room temperature overnight. Then, the reaction solution was filtered and evaporated. The residue was dissolved in 2 L of ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate), to give 106.6 g of (4S)-4-benzyl-3-(2-isopropoxyacetyl)-1,3-oxazolidin-2-one as a colorless oil.

Provenance & Evidence