Sodium Chloride → benzhydryl 7-formamido-3-[(Z)-2-(2-pyridyl)vinylthio]-3-cephem-4-carboxylate

HRID 704272Notes

Reaction equation

HRID 704272 reaction equation
[I-].[Na+].[CH:3]([NH:5][CH:6]1[C:34](=[O:35])[N:8]2[C:9]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:10](OS(C)(=O)=O)[CH2:11][S:12][C@H:7]12)=[O:4].[Cl-].[Na+].C(O[CH2:42][CH3:43])(=O)C>C(#N)C.[Ag]>[CH:3]([NH:5][CH:6]1[C:34](=[O:35])[N:8]2[C:9]([C:18]([O:20][CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:19])=[C:10]([S:12]/[CH:11]=[CH:10]\[C:43]3[CH:42]=[CH:34][CH:6]=[CH:7][N:8]=3)[CH2:11][S:12][C@H:7]12)=[O:4]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 88528775Benzhydryl 7-formamido-3-mesyloxy-3-cephem-4-carboxylate

Product 1

HCID 88528695benzhydryl 7-formamido-3-[(Z)-2-(2-pyridyl)vinylthio]-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of [(Z and E)-2-(2-pyridyl)vinylthio]silver (2.26 g) in acetonitrile (140 ml) was added sodium iodide (8.18 g) under ice-cooling. The mixture was stirred at the same temperature for 30 minutes. To this mixture was added benzhydryl 7-formamido-3-mesyloxy-3-cephem-4-carboxylate (4 g) at once at the same temperature. The mixture was stirred under ice-cooling for 30 minutes. The insoluble material was filtered off. The filtrate was concentrated in vacuo to give a residue. The residue was dissolved in a mixture of ethyl acetate and a saturated aqueous solution of sodium chloride. The mixture was stirred for 1 hour. Sellaite was added to the mixture. The insoluble material was filtered off. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to give a solid. The solid was subjected to column chromatography on silica gel (175 g) and eluted with a mixture of chloroform and ethyl acetate (4:1 v/v). The fractions containing the material having a larger Rf value in thin layer chromatography were combined and concentrated in vacuo to give benzhydryl 7-formamido-3-[(Z)-2-(2-pyridyl)vinylthio]-3-cephem-4-carboxylate (2.15 g) as a solid.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred under ice-
  3. temperaturecooling for 30 minutes
  4. filtrationThe insoluble material was filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a residue
  7. stirringThe mixture was stirred for 1 hour
  8. filtrationThe insoluble material was filtered off
  9. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customto give a solid
  13. washeluted with a mixture of chloroform and ethyl acetate (4:1 v/v)
  14. additionThe fractions containing the material
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1099dc6d2b34b5d8819167537578fef
Source dataset
uspto-grants-1991_01
Patent number
US04985555

Reaction notes

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