Ozone → HCID 12795886, compound

HRID 543598Notes

Reaction equation

HRID 543598 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.

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

Sources & evidence

ORD record
ord-199e4e2172154993a61c8c04c2bb93cc
Source dataset
uspto-grants-1984_05
Patent number
US04447360

Reaction notes

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