Sodium Iodide → HCID 14535682, compound

HRID 1905013Notes

Reaction equation

HRID 1905013 reaction equation
[I-].[Na+].[Cl:3][C:4]([Cl:51])([Cl:50])[CH2:5][O:6][C:7]([NH:9][C@@H:10]1[C:48](=[O:49])[N:12]2[C:13]([C:32]([O:34][CH:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])=[C:14](OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[CH2:15][S:16][C@H:11]12)=[O:8]>C(#N)C.[Ag].C(NC(/C=C\S)=O)C>[Cl:50][C:4]([Cl:51])([Cl:3])[CH2:5][O:6][C:7]([NH:9][C@@H:10]1[C:48](=[O:49])[N:12]2[C:13]([C:32]([O:34][CH:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:33])=[C:14]([S:16]/[CH:11]=[CH:10]\[C:48](=[O:49])[NH:12][CH2:13][CH3:14])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 14535680HCID 14535680, compound

Product 1

HCID 14535682HCID 14535682, compoundYield 186.4%

Reagents, catalysts & solvents 2

HCID 88619285HCID 88619285, compoundCatalystHCID 6342AcetonitrileSolvent2×

Procedure

(a') To a suspension of 784 mg (3.294 mM) of (Z)-2-(N-ethylcarbamoyl)vinylmercaptan silver salt in 30 ml of acetonitrile was added 2.965 g (19.77 mM) of sodium iodide, and the mixture was stirred at room temperature for 5 minutes. To the mixture was added at 0° C. a solution of 2 g (2.53 mM) of benzhydryl 7β-2,2,2-trichloroethoxycarbonylamino-3-diphenylphosphoryloxy-3-cephem-4-carboxylate in 20 ml of acetonitrile, and the mixture was stirred at the same temperature for 30 minutes, and then some insoluble material was filtered. To the filtrate was added 100 ml of ethyl acetate, and the mixture was washed with a saturated aqueous sodium chloride solution (50 ml×3) and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was chromatographed over silica gel column (eluent; chloroform) to give 1.65 g of benzhydryl 7β-2,2,2-trichloroethyoxycarbonylamino-3-[(Z)-2-(N-ethylcarbamoyl)vinylthio]-3-cephem-4-carboxylate.

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. filtrationsome insoluble material was filtered
  3. additionTo the filtrate was added 100 ml of ethyl acetate
  4. washthe mixture was washed with a saturated aqueous sodium chloride solution (50 ml×3)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed over silica gel column (eluent; chloroform)

Sources & evidence

ORD record
ord-3e5a81b7764646f68ffe9266381da832
Source dataset
uspto-grants-1989_06
Patent number
US04841044

Reaction notes

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