Sodium Bicarbonate → Cefamandole sodium

HRID 1660638Notes

Reaction equation

HRID 1660638 reaction equation
[SH:1][C:2]1[N:6]([CH3:7])[N:5]=[N:4][N:3]=1.C(=O)([O-])O.[Na+:12].[C:13]([NH:23][C@@H:24]1[C:46](=[O:47])[N:26]2[C:27]([C:43]([OH:45])=[O:44])=[C:28]([CH2:31]OC(=O)C(C3C=CC=CC=3)O)[CH2:29][S:30][C@H:25]12)(=[O:22])[C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:15]>O>[Na+:12].[C:13]([NH:23][C@@H:24]1[C:46](=[O:47])[N:26]2[C:27]([C:43]([O-:45])=[O:44])=[C:28]([CH2:31][S:1][C:2]3[N:6]([CH3:7])[N:5]=[N:4][N:3]=3)[CH2:29][S:30][C@H:25]12)(=[O:22])[C@@H:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:15]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 131712065HCID 131712065, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 23672568Cefamandole sodium

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In water (5 ml) was dissolved 7β-(D-mandelamido)-3-mandelyloxymethyl-3-cephem-4-carboxylic acid (0.50 l g) together with 5-mercapto-1-methyl-1H-tetrazole (0.12 g) and sodium hydrogen carbonate (0.17 g). The solution was stirred at 60° C. for 30 minutes. After cooling in the air, the reaction mixture was subjected to column chromatography on Amberlite XAD-2, elution being carried out with water and a solvent mixture of water and methanol. The fractions containing the desired product were pooled, concentrated and lyophilized. The procedure provided 7β-(D-mandel-amido)-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid sodium salt (0.34 g).

Workup

  1. temperatureAfter cooling in the air
  2. washthe reaction mixture was subjected to column chromatography on Amberlite XAD-2, elution
  3. additiona solvent mixture of water and methanol
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54890b57e422414bb1cec8900a2cbae8
Source dataset
uspto-grants-1981_12
Patent number
US04308381

Reaction notes

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