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]-2-oxazolidinone in 150 cm3 of tetrahydrofuran and the mixture is stirred for 45 minutes at this temperature and then 7.72 cm3 of methyl iodide are added. The reaction mixture is then stirred for 15 hours at room temperature and then diluted with ethyl acetate, washed with 50 cm3 of water and then with 50 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is crystallized from isopropyl oxide, drained and dried. 4.2 g of (4S,5S)-4-methyl-5-phenyl-3-[(S)-2-(2-methoxyphenyl)-propionyl]-2-oxazolidinone are obtained in the form of a white solid.

Provenance & Evidence