Sodium Chloride → benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate

HRID 1723599Notes

Reaction equation

HRID 1723599 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]\[SH:9])[CH:2]=1.[I-].[Na+].[CH:12]1([O:15][N:16]=[C:17]([C:48]2[N:49]=[C:50]([NH:53][CH:54]=[O:55])[S:51][CH:52]=2)[C:18]([NH:20][C@@H:21]2[C:46](=[O:47])[N:23]3[C:24]([C:30]([O:32][CH:33]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])=[C:25]([CH2:28]Cl)[CH2:26][S:27][C@H:22]23)=[O:19])[CH2:14][CH2:13]1.[Cl-].[Na+]>C(#N)C.[Ag].C(OCC)(=O)C>[CH:12]1([O:15][N:16]=[C:17]([C:48]2[N:49]=[C:50]([NH:53][CH:54]=[O:55])[S:51][CH:52]=2)[C:18]([NH:20][C@@H:21]2[C:46](=[O:47])[N:23]3[C:24]([C:30]([O:32][CH:33]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])=[C:25]([CH2:28][S:9]/[CH:8]=[CH:7]\[C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH2:26][S:27][C@H:22]23)=[O:19])[CH2:14][CH2:13]1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 14705800(Z)-2-(3-pyridyl)ethenethiolHCID 131716070Benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 131716064benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylateYield 60.2%

Reagents, catalysts & solvents 3

HCID 23954SilverCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of silver salt of (Z)-2-(3-pyridyl)ethenethiol (2.03 g) and sodium iodide (3.36 g) in acetonitrile (40 ml) was stirred for 20 minutes at 0° C. in the dark. To the mixture was added benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (2.03 g) at -20° C., and the mixture was stirred at 0° C. for 1.5 hours. The mixture was poured into a mixture of saturated aqueous solution of sodium chloride (200 ml) and ethyl acetate (100 ml). The insoluble material was filtered off and the organic layer was separated. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether to give benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (1.41 g).

Workup

  1. stirringthe mixture was stirred at 0° C. for 1.5 hours
  2. filtrationThe insoluble material was filtered off
  3. customthe organic layer was separated
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8e12c1d2e87149a2bb531fee2562c9ce
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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