Reaktion #62782

Reaktionsgleichung

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

Ausbeute 42.4%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeevaporated
2. 2
   workup.ADDITIONTo the residue were added ethyl acetate (400 ml) and water (300 ml)
3. 3
   Sonstigethe organic layer was separated
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated
6. 6
   Waschenthe 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
   Sonstigeevaporated
10. 10
    SonstigeThe residue was triturated with diisopropyl ether

Vorschrift

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).

Quelle