Acetone → cefpodoxime sodium

HRID 989420Notes

Reaction equation

HRID 989420 reaction equation
C([O-])(=O)C.[Na+:5].[CH3:6][O:7][CH2:8][C:9]1[CH2:30][S:29][C@@H:12]2[C@H:13]([NH:16][C:17](/[C:19](/[C:23]3[N:27]=[C:26]([NH2:28])[S:25][CH:24]=3)=[N:20]\[O:21][CH3:22])=[O:18])[C:14](=[O:15])[N:11]2[C:10]=1[C:31]([OH:33])=[O:32].CN(C)C(=O)C.CC(C)=O>O.CO>[CH3:6][O:7][CH2:8][C:9]1[CH2:30][S:29][C@@H:12]2[C@H:13]([NH:16][C:17](/[C:19](/[C:23]3[N:27]=[C:26]([NH2:28])[S:25][CH:24]=3)=[N:20]\[O:21][CH3:22])=[O:18])[C:14](=[O:15])[N:11]2[C:10]=1[C:31]([O-:33])=[O:32].[Na+:5]

Participants

7

Reactant 4

HCID 180AcetoneHCID 31374DimethylacetamideHCID 517045Sodium AcetateHCID 6335986Cefpodoxime

Product 1

HCID 23669317cefpodoxime sodiumYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.01 g of sodium acetate was dissolved in a mixture of 1 ml of water and 5 ml of methanol, and 5.0 g of cefpodoxime was added thereto, followed by addition of 15 ml of N,N-dimethylacetamide. The mixture was stirred at room temperature for 30 minutes and then, 100 ml of acetone was added thereto. The solution was stirred for 20 minutes and filtered. The filtered solid was washed with 50 ml of acetone and then with 30 ml of isopropyl ether, and vacuum-dried at room temperature to give 5.04 g of pale yellow cefpodoxime sodium salt (yield: 96%).

Workup

  1. additionwas added
  2. stirringThe solution was stirred for 20 minutes
  3. filtrationfiltered
  4. washThe filtered solid was washed with 50 ml of acetone
  5. dry with materialwith 30 ml of isopropyl ether, and vacuum-dried at room temperature

Sources & evidence

ORD record
ord-bc90c490d620440cab7eef9ecb548d4b
Source dataset
uspto-grants-2003_10
Patent number
US06639068B1

Reaction notes

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