Ozone → HCID 12795886, compound

HRID 1065835Notes

Reaction equation

HRID 1065835 reaction equation
[O:1]=[O+][O-].[CH3:4][O:5][C:6](=[O:20])[C:7]([N:11]1[C@H:14]([S:15][C:16](=[O:18])[CH3:17])[CH2:13][C:12]1=[O:19])=C(C)C>CO>[CH3:4][O:5][C:6](=[O:20])[C:7]([N:11]1[C@H:14]([S:15][C:16](=[O:18])[CH3:17])[CH2:13][C:12]1=[O:19])=[O:1]

Participants

4

Reactant 2

HCID 24823OzoneHCID 12795451HCID 12795451, compound

Product 1

HCID 12795886HCID 12795886, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 equivalents of ozone are introduced over a period of 60 minutes into a solution, cooled to -15°, of 150 mg of 2-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-3-methylcrotonic acid methyl ester in 3 ml of methanol. The reaction mixture is rinsed with nitrogen, diluted with methylene chloride and washed for 2 minutes with a 5% aqueous sodium bisulphite solution. The organic phase is dried over sodium sulphate and concentrated in vacuo. IR spectrum of the resulting oily title compound (in methylene chloride): characteristic bands at 3.30-3.40, 5.52, 5.70, 5.83 (sh), 5.86, 6.98, 7.08 (sh), 7.40, 7.82-8.00 (broad, sh), 8.07, 8.19, 8.30 (sh), 8.46, 8.90, 9.22, 9.52, 9.91, 10.30 and 10.73μ. The product obtained can be used in the next stage without further purification.

Workup

  1. washThe reaction mixture is rinsed with nitrogen
  2. additiondiluted with methylene chloride
  3. washwashed for 2 minutes with a 5% aqueous sodium bisulphite solution
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe product obtained can
  7. custombe used in the next stage without further purification

Sources & evidence

ORD record
ord-c7459c67ad8c4b96be2fc5c79065053b
Source dataset
uspto-grants-1982_05
Patent number
US04331676

Reaction notes

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