Reaction #93025

ord-3d28ec22631c49fbb7e9d1fa971a4369

Reaction equation

O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid
O=C(Cc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)C(C=C(Cl)Cl)=CS[C@H]12
benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-2-cephem-4-carboxylate
→
O=C(Cc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(C=C(Cl)Cl)CS(=O)[C@H]12
benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate-1-oxide
Yield 42.6%

Reactants

O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid
O=C(Cc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)C(C=C(Cl)Cl)=CS[C@H]12
benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-2-cephem-4-carboxylate

Reagents

None

Solvents

CCOC(C)=O
ethyl acetate
CCOC(C)=O
ethyl acetate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturecooling
  2. 2
    FiltrationThe precipitates were collected by filtration

Procedure

A solution of m-chloroperbenzoic acid (7 g) in ethyl acetate (35 ml) was added to a solution of benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-2-cephem-4-carboxylate (15 g) in ethyl acetate (75 ml) under ice-cooling and the mixture was stirred at the same temperature for an hour. The precipitates were collected by filtration to give benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate-1-oxide (6.57 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04609730uspto-grants-1986_09