Sodium Bicarbonate → Cefazolin Sodium

HRID 261720Notes

Reaction equation

HRID 261720 reaction equation
[SH:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][N:3]=1.C(=O)([O-])O.[Na+:12].[N:13]1([CH2:18][C:19]([NH:21][C@@H:22]2[C:51](=[O:52])[N:24]3[C:25]([C:48]([OH:50])=[O:49])=[C:26]([CH2:29]OC(=O)C4C=CC=CC=4S(=O)(=O)NC(OCC)=O)[CH2:27][S:28][C@H:23]23)=[O:20])[CH:17]=[N:16][N:15]=[N:14]1>P([O-])([O-])([O-])=O>[N:13]1([CH2:18][C:19]([NH:21][C@@H:22]2[C:51](=[O:52])[N:24]3[C:25]([C:48]([O-:50])=[O:49])=[C:26]([CH2:29][S:1][C:2]4[S:6][C:5]([CH3:7])=[N:4][N:3]=4)[CH2:27][S:28][C@H:23]23)=[O:20])[CH:17]=[N:16][N:15]=[N:14]1.[Na+:12]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 705840957beta-(1H-tetrazol-1-yl)acetamido-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acidHCID 178434161HCID 178434161, compound

Product 1

HCID 23675322Cefazolin Sodium

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

In a phosphate buffer solution of pH 6.4 (3 ml) are dissolved 5-mercapto-2-methyl-1,3,4-thiadiazole (79 mg), sodium hydrogen carbonate (92 mg) and 7β-(1H-tetrazol-1-yl)acetamido-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (298 mg) and the resultant solution is heated at 60° C. for one hour. Then, the mixture is concentrated and the residue is subjected to column chromatography on Sephadex LH-20, elution being carried out with water. The fractions containing the desired product are pooled and lyophilized. The procedure provides sodium 7β-(1H-tetrazol-1-yl)acetamido-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate. This product is in good agreement with the authentic sample in NMR spectrum.

Workup

  1. concentrationThen, the mixture is concentrated
  2. washthe residue is subjected to column chromatography on Sephadex LH-20, elution
  3. additionThe fractions containing the desired product

Sources & evidence

ORD record
ord-33b5df6cb4fd4e98814297962d885158
Source dataset
uspto-grants-1979_08
Patent number
US04166178

Reaction notes

Loading…