Ammonium Chloride → HCID 67232581, compound

Participants

Reaction Steps

To a solution of the compound (2.5 g) obtained in step 3 in THF (180 mL) were added at −78° C. pivaloyl chloride (12.9 g) and triethylamine (2.25 g) and the mixture was stirred for 2 hr. To this mixture was added at −78° C. a solution of oxazolidinone lithium anion (prepared by adding n-butyllithium (2.5M hexane solution, 5.34 mL) to (R)-4-benzyloxazolidin-2-one (1.73 g) in THF (180 mL) at −78° C. and stirring for 1 hr), and the mixture was stirred at room temperature for 18 hr. The reaction was discontinued by adding saturated aqueous ammonium chloride solution (200 mL), and the mixture was extracted with ethyl acetate (300 mL). The extract was dried, concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (25% ethyl acetate/hexane) to give (4R)-4-benzyl-3-[(2E)-3-(5-fluoropyridin-2-yl)prop-2-enoyl]-1,3-oxazolidin-2-one (2.3 g, 80%) as a pale-yellow oil.

Provenance & Evidence