Sodium Thiosulfate → trans-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

HRID 231230Notes

Reaction equation

HRID 231230 reaction equation
ClC1C=CC=[C:4]([C:8](OO)=[O:9])C=1.C([C@@H:15]1[NH:18][C:17](=[O:19])[C@H:16]1[CH:20]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH3:21])(=O)C.S([O-])([O-])(=[O:32])=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:8]([O:19][C@@H:17]1[NH:18][C:15](=[O:32])[C@H:16]1[CH:20]([O:22][Si:23]([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:24])[CH3:25])[CH3:21])(=[O:9])[CH3:4]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67789308trans-4-Acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

Product 1

HCID 67757824trans-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

m-Chloroperbenzoic acid (1 g) is added to a solution of trans-4-acetyl-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone (0.23 g) in chloroform (15 ml), and the mixture is allowed to stand at room temperature for 15 hours and then poured into a mixture of ethyl acetate (100 ml), 5% aqueous sodium thiosulfate (50 ml) and aqueous sodium hydrogen carbonate (30 ml). The organic layer is separated, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to give 0.23 g of trans-4-acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone.

Workup

  1. customThe organic layer is separated
  2. washwashed with aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a11fd0963f54f2b8573806da77e1ad0
Source dataset
uspto-grants-1989_07
Patent number
US04845210

Reaction notes

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