Reacción #62776

Ecuación de reacción

water

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

sodium iodide

3-mercapto-4-methyl-5-oxo-6-hydroxy-4,5-dihydro-1,2,4-triazine

→

benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(4-methyl-5-oxo-6-hydroxy-4,5-dihydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylate

Rendimiento 73.1%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting precipitates
2. 2
   Filtraciónwere collected by filtration
3. 3
   workup.DISSOLUTIONdissolved in ethyl acetate
4. 4
   LavadoThe solution was washed with water
5. 5
   Secadoan aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride successively, dried
6. 6
   Otroevaporated under reduced pressure
7. 7
   OtroThe residue was triturated in diisopropyl ether
8. 8
   Filtracióncollected by filtration

Procedimiento

To a mixture of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (1.5 g) and sodium iodide (769 mg) in N,N-dimethylformamide was added 3-mercapto-4-methyl-5-oxo-6-hydroxy-4,5-dihydro-1,2,4-triazine (816 mg). After being stirred for 45 minutes at room temperature, the reaction mixture was poured into water. The resulting precipitates were collected by filtration and dissolved in ethyl acetate. The solution was washed with water, an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride successively, dried and evaporated under reduced pressure. The residue was triturated in diisopropyl ether and collected by filtration to give benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(4-methyl-5-oxo-6-hydroxy-4,5-dihydro-1,2,4-triazin-3-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (1.25 g).

Fuente