Hydrogen Peroxide → 2-[8-(2-Methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyric acid

Participants

Reaction Conditions

Reaction Steps

122 ml of hydrogen peroxide (30%) are added dropwise and then 0.17 g of lithium hydroxide monohydrate is added to the solution of 0.95 g of 4(R)-benzyl-3-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyryl}oxazolidin-2-one in 12 ml of tetrahydrofuran and 4 ml of water at 0° C. After 6 hours at room temperature, the reaction mixture is cooled to 0° C. and admixed with a solution of 1.54 g of sodium sulphite in 9 ml of water (negative peroxide test). The reaction mixture is adjusted to pH 9.8 with saturated aqueous sodium hydrogen-carbonate solution and clarified by filtration, and the tetrahydrofuran is concentrated by evaporation. The residue is washed with dichloromethane (3×)—the combined organic phases are washed with phosphate buffer/25% conc. ammonia solution (pH 9.8). The combined aqueous phases are adjusted to pH 3.0 with 4N HCl and extracted with dichloromethane (2×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The crude title compound is identified on the basis of the Rf value from the residue.

Provenance & Evidence