Réaction #62781

Équation de réaction

sodium bisulfite

sodium bicarbonate

benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

m-chloroperbenzoic acid

→

benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide

Rendement 84.0%

Solvants

water

ethyl acetate

Conditions de réaction

Traitement

1. 1
   AutreThe organic layer was separated
2. 2
   Lavagewashed with an aqueous solution of sodium chloride
3. 3
   Séchagedried over magnesium sulfate
4. 4
   Autreevaporated
5. 5
   AutreThe residue was triturated with diisopropyl ether

Mode opératoire

A mixture of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (35 g), m-chloroperbenzoic acid (8.64 g) and ethyl acetate (300 ml) was stirred for 30 minutes at 0° to 5° C. and then, water (300 ml), sodium bisulfite and sodium bicarbonate were added thereto. The organic layer was separated, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated. The residue was triturated with diisopropyl ether to give benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (29.93 g).

Source