Sodium Iodide → Benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-carbamoyl-1-pyridinio)methyl-3-cephem-4-carboxylate 1-oxide iodide

HRID 1074362Notes

Reaction equation

HRID 1074362 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:38]2[N:39]=[C:40]([NH:43][CH:44]=[O:45])[S:41][CH:42]=2)[C:7]([NH:9][C@@H:10]2[C:36](=[O:37])[N:12]3[C:13]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])=[C:14]([CH2:18]Cl)[CH2:15][S:16](=[O:17])[C@H:11]23)=[O:8])[CH2:3][CH2:2]1.[I-:46].[Na+].[C:48]([NH2:56])(=[O:55])[C:49]1[CH:54]=[CH:53][N:52]=[CH:51][CH:50]=1.C(OC(C)C)(C)C>CN(C)C=O>[I-:46].[CH:1]1([O:4][N:5]=[C:6]([C:38]2[N:39]=[C:40]([NH:43][CH:44]=[O:45])[S:41][CH:42]=2)[C:7]([NH:9][C@@H:10]2[C:36](=[O:37])[N:12]3[C:13]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])=[C:14]([CH2:18][N+:52]4[CH:53]=[CH:54][C:49]([C:48](=[O:55])[NH2:56])=[CH:50][CH:51]=4)[CH2:15][S:16](=[O:17])[C@H:11]23)=[O:8])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7914Diisopropyl EtherHCID 15074IsonicotinamideHCID 131716071Benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate 1-oxide

Product 1

HCID 131716072Benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-carbamoyl-1-pyridinio)methyl-3-cephem-4-carboxylate 1-oxide iodide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate 1-oxide (syn isomer) (2.5 g) and sodium iodide (3.4 g) in N,N-dimethylformamide (20 ml) was stirred at ambient temperature for 30 minutes. To the mixture was added isonicotinamide (0.91 g) under ice-cooling and the mixture was stirred for 2 hours at the same temperature. The mixture was poured into diisopropyl ether to give an oil. The oil was separated by decantation and triturated with water. The solid was dissolved in tetrahydrofuran, dried over magnesium sulfate, concentrated under reduced pressure, and triturated in diisopropyl ether to give benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-carbamoyl-1-pyridinio)methyl-3-cephem-4-carboxylate 1-oxide iodide (syn isomer) as a solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hours at the same temperature
  3. customto give an oil
  4. customThe oil was separated by decantation
  5. customtriturated with water
  6. dissolutionThe solid was dissolved in tetrahydrofuran
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customtriturated in diisopropyl ether

Sources & evidence

ORD record
ord-73d350c201d94bdeb384783d4a8a0494
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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