Sodium periodate → HCID 58844200, compound

Participants

Reaction Steps

(3S,4R)-3-((1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-4-{2-[3-(2-hydroxyethyl)phenyl]-2-oxoethyl}azetidin-2-one (3.0 g) prepared by reference example 15 and ruthenium trichloride (79 mg) were dissolved in acetone (77 ml) and to the solution was added at room temperature a solution of sodium periodate (3.3 g) in water (40 ml). The solution was stirred for 30 minutes. Further, a solution of sodium periodate (0.66 g) in water (4 ml) was added thereto and the solution was stirred for 3 hours. After removal of insoluble materials by filtration with celite, acetone was removed under reduced pressure. To the aqueous layer (about 50 ml) was added a saturated aqueous sodium chloride solution (100 ml) and the mixture was extracted with ethyl acetate (3×50 ml). The organic layers were combined, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to give (3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidin-2-yl]acetyl}phenyl)acetic acid (2.72 g).

Provenance & Evidence