Acetic Acid → HCID 57271238, compound

Participants

Reaction Steps

To a solution, cooled to -50° C., of 22.82 g of (4R, 5R)-4-methyl-5-phenyl-3-[(2-methoxyphenyl)acetyl]-2-oxazolidinone in 190 cm3 of tetrahydrofuran are added 19.31 g of sodium 1,1,1,3,3,3-hexamethyldisilazide, and the mixture is stirred for 45 minutes at this temperature, followed by addition of 8.82 cm3 of methyl iodide. The reaction mixture is subsequently stirred for 15 hours at room temperature, and then 18.65 cm3 of acetic acid are added, and the mixture is diluted with 200 cm3 of ethyl acetate and washed with 200 cm3 of water and then with 250 cm3 of saturated aqueous sodium chloride solution, and dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is crystallized in isopropyl ether, filtered off and dried. 10.95 g of (4R, 5R)-4-methyl-5-phenyl-3-[(R)-2-(2-methoxyphenyl)propionyl]-2-oxazolidinone are obtained, in the form of a white solid melting at 110° C.

Provenance & Evidence