Methyl iodide → (4S,5S)-4-methyl5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]2-oxazolidinone

Participants

Reaction Steps

19.1 g of sodium 1,1,1,3,3,3-hexamethyldisilazanate are added to a solution, cooled to -50° C., of 10 g of (4S,5S)-4-methyl-5-phenyl-3-[(2-methoxyphenyl)-acetyl]-oxazolidin-2-one in 150 cm3 of tetrahydrofuran, the mixture is stirred at this temperature for 45 minutes and 7.72 cm3 of methyl iodide are then added. The reaction mixture is subsequently stirred at room temperature for 15 hours and then diluted with ethyl acetate, washed with 50 cm3 of water and then with 50 cm3 of an aqueous saturated solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is crystallised in isopropyl ether, filtered off and dried. 4.2 g of (4S,5S)-4-methyl-5-phenyl-3-[2-(2-methoxyphenyl)-(S)-propionyl]-oxazolidin-2-one are obtained in the form of a white solid.

Provenance & Evidence