Ozone → 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-oxoacetic acid 2,2,2-trichloroethyl ester

HRID 2309086Notes

Reaction equation

HRID 2309086 reaction equation
[O:1]=[O+][O-].[Cl:4][C:5]([Cl:26])([Cl:25])[CH2:6][O:7][C:8](=[O:24])[C:9]([N:13]1[C@H:16]([S:17][C:18](=[O:20])[CH3:19])[C@@H:15]([O:21][CH3:22])[C:14]1=[O:23])=C(C)C>C(OC)(=O)C>[Cl:4][C:5]([Cl:26])([Cl:25])[CH2:6][O:7][C:8](=[O:24])[C:9]([N:13]1[C@H:16]([S:17][C:18](=[O:20])[CH3:19])[C@@H:15]([O:21][CH3:22])[C:14]1=[O:23])=[O:1]

Participants

4

Reactant 2

HCID 24823Ozone2×HCID 867417812-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-3-methylcrotonic acid 2,2,2-trichloroethyl ester

Product 1

HCID 867417832-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-oxoacetic acid 2,2,2-trichloroethyl ester

Reagents, catalysts & solvents 1

HCID 6584Methyl AcetateSolvent

Procedure

3 equivalents of ozone are conveyed through a solution, cooled to -30°, of 8.4 g of 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-3-methylcrotonic acid 2,2,2-trichloroethyl ester in 765 ml of methyl acetate. After treating with ozone, the reaction mixture is left to stand at the same temperature for 15 minutes and then the excess ozone is removed by a nitrogen current. The reaction mixture is washed at 0° with a 10% aqueous sodium bisulphite solution and then with sodium chloride solution. After separating off, the combined aqueous phases are extracted a further 4 times with methyl acetate. The combined methyl ester solutions are dried over sodium sulphate and concentrated by evaporation in vacuo.

Workup

  1. waitthe reaction mixture is left
  2. customthe excess ozone is removed by a nitrogen current
  3. washThe reaction mixture is washed at 0° with a 10% aqueous sodium bisulphite solution
  4. customAfter separating off
  5. extractionthe combined aqueous phases are extracted a further 4 times with methyl acetate
  6. dry with materialThe combined methyl ester solutions are dried over sodium sulphate
  7. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-e1cf0558802f4f3dbe1974055b563d78
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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