Sodium periodate → HCID 58844200, compound

HRID 1271116Notes

Reaction equation

HRID 1271116 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][OH:26])[CH:19]=2)=[O:17])[NH:13][C:12]1=[O:27])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:29].[Na+]>CC(C)=O.O.[Ru](Cl)(Cl)Cl>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:12](=[O:27])[NH:13][C@@H:14]1[CH2:15][C:16]([C:18]1[CH:19]=[C:20]([CH2:24][C:25]([OH:29])=[O:26])[CH:21]=[CH:22][CH:23]=1)=[O:17])[CH3:10])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 23667635Sodium periodate2×HCID 58844243HCID 58844243, compound

Product 1

HCID 58844200HCID 58844200, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

(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).

Workup

  1. stirringthe solution was stirred for 3 hours
  2. customAfter removal of insoluble materials
  3. filtrationby filtration with celite, acetone
  4. customwas removed under reduced pressure
  5. additionTo the aqueous layer (about 50 ml) was added a saturated aqueous sodium chloride solution (100 ml)
  6. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9f0dfee012874691a656a3fdebf677ce
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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