Ozone → alpha-[4-Acetylthio-3-phthalimido-2-oxoazetidin-1-yl]-alpha-acetylacetic acid

HRID 971532Notes

Reaction equation

HRID 971532 reaction equation
[C:1]([S:4][CH:5]1[N:8]([CH:9]([C:13]([CH3:15])=C)[C:10]([OH:12])=[O:11])[C:7](=[O:16])[CH:6]1[N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])(=[O:3])[CH3:2].[O:28]=[O+][O-]>CO>[C:1]([S:4][CH:5]1[N:8]([CH:9]([C:13](=[O:28])[CH3:15])[C:10]([OH:12])=[O:11])[C:7](=[O:16])[CH:6]1[N:17]1[C:18](=[O:27])[C:19]2=[CH:26][CH:25]=[CH:24][CH:23]=[C:20]2[C:21]1=[O:22])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24823OzoneHCID 20464336alpha-[4-Acetylthio-3-phthalimido-2-oxoazetidin-1-yl]-alpha-isopropenyl acetic acid

Product 1

HCID 20464401alpha-[4-Acetylthio-3-phthalimido-2-oxoazetidin-1-yl]-alpha-acetylacetic acidYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of α-[4 -acetylthio-3-phthalimido-2-oxoazetidin-1-yl]-α-isopropenyl acetic acid (100 mg) in methanol (10 ml) at 0° C. is introduced excess ozone. After the gas at the outlet makes a potassium iodide starch paper coloured, the reaction mixture is bubbled with sulfur dioxide gas. The reaction mixture is concentrated, and the obtained residue is dissolved in aqueous solution of sodium hydrogen carbonate, washed with ether, neutralized with hydrochloric acid, and extracted with methylene chloride. The extract solution is washed with water, dried, and evaporated to give α-[4-acetylthio-3-phthalimido-2-oxoazetidin-1-yl]-α-acetylacetic acid (64 mg). Yield: 63%. Foam. IR: νmaxCHCl3 1780, 1730, 1680 cm-1.

Workup

  1. customthe reaction mixture is bubbled with sulfur dioxide gas
  2. concentrationThe reaction mixture is concentrated
  3. dissolutionthe obtained residue is dissolved in aqueous solution of sodium hydrogen carbonate
  4. washwashed with ether
  5. extractionextracted with methylene chloride
  6. washThe extract solution is washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-9e6ab166918f4f888c3fa8b5bb5338fb
Source dataset
uspto-grants-1979_07
Patent number
US04160085

Reaction notes

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