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

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Reaction Steps

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 are added 19.1 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 7.72 cm3 of methyl iodide. The reaction mixture is subsequently stirred for 15 hours at room temperature, and then diluted with ethyl acetate and washed with 50 cm3 of water followed by 50 cm3 of saturated aqueous sodium chloride solution, 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. 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