Reaction #54380

ord-d47c3424e7734792bd9437dc73a0a2de

Reaction equation

O=[O+][O-]
ozone
CSC
dimethyl sulphide
C/C(O)=C(/C(=O)OCC(Cl)(Cl)Cl)N1C(=O)C(NC(=O)COc2ccccc2)C1SSc1nc2ccccc2s1
2-[4-(benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1 -yl]-3-hydroxy-crotonic acid 2,2,2-trichloroethyl ester
→
C=C(C)C(C(=O)OCC(Cl)(Cl)Cl)N1C(=O)C(NC(=O)COc2ccccc2)C1SSc1nc2ccccc2s1
2-[4-(benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylene-butyric acid 2,2,2-trichloroethyl ester

Reactants

—
ozonide
O=[O+][O-]
ozone
CSC
dimethyl sulphide
C/C(O)=C(/C(=O)OCC(Cl)(Cl)Cl)N1C(=O)C(NC(=O)COc2ccccc2)C1SSc1nc2ccccc2s1
2-[4-(benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1 -yl]-3-hydroxy-crotonic acid 2,2,2-trichloroethyl ester

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Analogously to Example 6a), 647 mg (1 mM) of 2-[4-(benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylene-butyric acid 2,2,2-trichloroethyl ester and 1.2 equivalents of ozone, with subsequent splitting of the ozonide with dimethyl sulphide, give 2-[4-(benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1 -yl]-3-hydroxy-crotonic acid 2,2,2-trichloroethyl ester; melting point 129-130° C. (ether/petroleum ether).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04147864uspto-grants-1979_04