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

HRID 1155443Notes

Reaction equation

HRID 1155443 reaction equation
O=[O+][O-].[CH3:4]SC.[Cl:7][C:8]([Cl:45])([Cl:44])[CH2:9][O:10][C:11](=[O:43])/[C:12](/[N:16]1[CH:19]([S:20][S:21][C:22]2[S:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[CH:18]([NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:17]1=[O:42])=[C:13](\O)/[CH3:14]>>[Cl:44][C:8]([Cl:7])([Cl:45])[CH2:9][O:10][C:11](=[O:43])[CH:12]([N:16]1[CH:19]([S:20][S:21][C:22]2[S:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[CH:18]([NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:17]1=[O:42])[C:13](=[CH2:4])[CH3:14]

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 867364492-[4-(Benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-hydroxy-crotonic acid 2,2,2-trichloroethyl ester

Product 1

HCID 128952462-[4-(Benzthiazol-2-yldithio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylene-butyric acid 2,2,2-trichloroethyl ester

Procedure

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).

Sources & evidence

ORD record
ord-47a595e779774cfdaa7b4784077c0686
Source dataset
uspto-grants-1981_11
Patent number
US04301278

Reaction notes

Loading…