Phenylacetic Acid → HCID 11066354, compound

Participants

Reaction Conditions

Reaction Steps

A mechanically stirred solution of phenylacetic acid at -78° C. is treated with one part pivaloyl chloride then one part triethylamine. The mixture is stirred at -78° C. for 15 minutes, at 0° C. for 45 minutes, then recooled to -78° C. In a separate flask, one part 2.5M nBuLi is added to a solution of (4S,5R)-(-)-4-methyl-5-phenyl-2-oxazolidinone in THF at -78° C. The solution is stirred for 15 minutes then transferred to the flask containing pivalic anhydride via cannula. The mixture is stirred for 15 minutes at -78° C. and 9 hours at room temperature. The mixture is quenched with 2M KHSO4 and, after evaporation of the THF, is extracted 3 times with ethyl acetate. The combined ethyl acetate extracts are dried over MgSO4, filtered and concentrated to provide the crude title compound which is purified by column chromatography eluting with ethyl acetate-hexane.

Provenance & Evidence