Dimethyl Sulfide → 2-[4-(Benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylene-butyric acid 2,2,2-trichloroethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Dimethyl Sulfide	HCID 1068	—
Reactant	Ozone	HCID 24823	—
Reactant	2-[4-(Benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-hydroxy-crotonic acid 2,2,2-trichloroethyl ester	HCID 86736449	—
Product	2-[4-(Benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylene-butyric acid 2,2,2-trichloroethyl ester	HCID 12895246	—

Reaction Steps

Analogously to Example 6(a), 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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04301278
Source dataset	uspto-grants-1981_11
ORD ID	ord-47a595e779774cfdaa7b4784077c0686
Source note	uspto-grants-1981_11