Sodium Bicarbonate → Cefamandole sodium

HRID 1389682Notes

Reaction equation

HRID 1389682 reaction equation
[C:1]([NH:11][C@@H:12]1[C:34](=[O:35])[N:14]2[C:15]([C:31]([OH:33])=[O:32])=[C:16]([CH2:19]OC(=O)C(C3C=CC=CC=3)O)[CH2:17][S:18][C@H:13]12)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[SH:36][C:37]1[N:41]([CH3:42])[N:40]=[N:39][N:38]=1.C(=O)([O-])O.[Na+:47]>O>[Na+:47].[C:1]([NH:11][C@@H:12]1[C:34](=[O:35])[N:14]2[C:15]([C:31]([O-:33])=[O:32])=[C:16]([CH2:19][S:36][C:37]3[N:41]([CH3:42])[N:40]=[N:39][N:38]=3)[CH2:17][S:18][C@H:13]12)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

5

Reactant 3

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

Product 1

HCID 23672568Cefamandole sodiumYield 70%

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 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-mandelamido)-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-ec16a2cb2e164fc99d49990a64226ce3
Source dataset
uspto-grants-1981_01
Patent number
US04245088

Reaction notes

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