Citric Acid → HCID 59659329, compound

Participants

Reaction Steps

A mixed solvent of tetrahydrofuran (60 mL) and distilled water (20 mL) was added with a 2 mol/L aqueous lithium hydroxide solution (4.5 mL, 8.8 mmol) and 30 wt % of hydrogen peroxide (3.9 mL, 35.2 mmol) at 0° C., and the mixture was further added with a tetrahydrofuran (30 mL) solution of N-[4-(3-(4(S)-benzyl-oxooxazolidine-3-yl)-2(S)-{3-[(2,2-dimethylpropionyl)isobutylamino]-4-methoxyphenyl}-3-oxopropyl)phenyl]-2,6-dichlorobenzamide (3.3 g, 4.4 mmol), and was then stirred for 30 minutes. After the reaction, the solution was added with a saturated aqueous sodium hydrogen sulfite solution (42 mL) and a 10 wt % aqueous citric acid solution (33 mL), stirred for 30 minutes, extracted with ethyl acetate (100 mL×2), and the extract was dried over anhydrous magnesium sulfate. The dried organic phase was filtered, the filtrate was concentrated under reduced pressure, and the resultant residue was purified through silica gel column chromatography (n-hexane:ethyl acetate (v/v)=2:1) to thereby obtain 3-[4-(2,6-dichlorobenzoyl amino)phenyl]-2(S)-{3-[(2,2-dimethylpropionyl)isobutyl amino]-4-methoxyphenyl}propionic acid (yield: 1.3 g, yield ratio: 50%).

Provenance & Evidence