Reacción #62782

Ecuación de reacción

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

sodium iodide

→

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

Rendimiento 42.4%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated
2. 2
   workup.ADDITIONTo the residue were added ethyl acetate (400 ml) and water (300 ml)
3. 3
   Otrothe organic layer was separated
4. 4
   Otrodried
5. 5
   Otroevaporated
6. 6
   Lavadothe elution
7. 7
   workup.ADDITIONwas carried out with a mixture of chloroform and ethyl acetate (15:1)
8. 8
   workup.ADDITIONThe fractions containing the object compound
9. 9
   Otroevaporated
10. 10
    OtroThe residue was triturated with diisopropyl ether

Procedimiento

A mixture of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (29 g), sodium iodide (14.6 g) and acetone (300 ml) was stirred for 2.0 hours at 0°-5° C. and evaporated. To the residue were added ethyl acetate (400 ml) and water (300 ml), and the organic layer was separated, dried and evaporated. The residue was subjected to column chromatography on silica gel (600 g) and the elution was carried out with a mixture of chloroform and ethyl acetate (15:1). The fractions containing the object compound were combined and evaporated. The residue was triturated with diisopropyl ether to give benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-iodomethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (13.57 g).

Fuente