Hydrogen Peroxide → HCID 24963431, compound

Participants

Reaction Steps

1.535 g of 4 (S)-Benzyl-3-[3-(3-hydroxyphenyl)-2 (S)-isopropoxypropionyl]oxazolidin-2-one was dissolved in 40 ml of tetrahydrofuran, and 3.3 ml of 30% aqueous hydrogen peroxide and 12 ml of 1N aqueous lithium hydroxide were successively added under ice-cooling, and stirring was continued at room temperature overnight. After adding water to the reaction solution, the mixture was extracted with dichloromethane and the aqueous layer was acidified by 1N hydrochloric acid. Following extraction (×3) was conducted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressures, to give 847 mg of 3-(3-hydroxyphenyl)-2(S)-isopropoxypropanoic acid. This product was then dissolved in 10 ml of N,N-dimethylformamide, and 400 mg of potassium hydrogencarbonate and 0.32 ml of ethyl iodide were successively added thereto, and stirring was continued at room temperature for 3 days. The reaction solution was diluted with ethylacetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 567 mg of the title compound as a colorless oil in the 3:1 hexane-ethyl acetate fraction.

Provenance & Evidence