Hydrogen Peroxide → (S)-4-Benzyl-3-[(2S,3R)-3-(4-benzyloxyphenyl)-3-hydroxy-2-(4-methylphenoxy)propionyl]oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A 1M solution of dibutylboron triflate in dichloromethane (33.2 ml) and triethylamine (5.12 ml) were added at 0° C. to a solution of (S)-4-benzyl-3-[(4-methylphenoxy)acetyl]oxazolidin-2-one (9.00 g) obtained from Reference example 20(a) in dichloromethane (90 ml), and the mixture was stirred at 0° C. for 1 hour. A solution of 4-benzyloxybenzaldehyde (6.46 g) in dichloromethane (6 ml) was added dropwise at −78° C. to the reaction solution, and then the reaction solution was stirred at 0° C. for 2 hours. A mixed solution (20 ml) of a saturated aqueous sodium chloride solution and methanol (1:1) and a mixed solution (100 ml) of an aqueous solution of hydrogen peroxide (31%) and methanol (2:1) were added thereto, and the resulting reaction solution was stirred for 1 hour. After the methanol was evaporated under reduced pressure, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed successively with an aqueous solution of hydrochloric acid (1N), a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluant; hexane/ethyl acetate=3/1˜1/1) to afford the target compound (9.80 g) as a foam.

Provenance & Evidence