Hydrogen Peroxide → HCID 9822765, compound

Participants

Reaction Steps

The (4S)-3-[2-ethyl-3-[4-methoxy-3-[[N-[4-(trifluoromethyl)phenyl]carbamoyl]methyl]phenyl]propanoyl]-4-benzyloxazolidine-2-one with high polarity (2.65 g, 4.66 mmol) was dissolved into a mixed solvent (4:1 v/v) (23 mL) of tetrahydrofuran with water, and cooled with ice after replacement with argon. Under stirring, 30% aqueous hydrogen peroxide (1.89 mL, 18.6 mmol) was added dropwise over 5 minutes. Following this, lithium hydroxide monohydrate (313 mg, 7.46 mmol) dissolved into water (7.8 mL) was added dropwise over 5 minutes, and the mixture was stirred further for 4 hours under cooling with ice. To the reaction mixture, 64% sodium hydrogensulfite (2.98 g, 18.6 mmol) dissolved into water (12 mL) was added dropwise. The reaction mixture was concentrated and the residue was poured into ice water, which was made acidic by adding 5% hydrochloric acid, and then extracted with methylene chloride. The extracte was washed with brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was dissolved into isopropyl ether under heating and allowed to stand. The precipitated crystals were collected by filtration and dried. Further, after concentration, the filtrate was purified by silica gel column chromatography (eluent: methylene chloride:methanol=20:1→15:1 v/v) to afford 1.37 g (72%) of (+)-2-ethyl-3-[4-methoxy-3-[[N-[4-(trifluoromethyl)-phenyl]carbamoyl]methyl]phenyl]propanoic acid as colorless crystalline powder.

Provenance & Evidence