Cefpodoxime → cefpodoxime sodium

HRID 989419Notes

Reaction equation

HRID 989419 reaction equation
C(C(CCCC)C([O-])=O)C.[Na+:11].[CH3:12][O:13][CH2:14][C:15]1[CH2:36][S:35][C@@H:18]2[C@H:19]([NH:22][C:23](/[C:25](/[C:29]3[N:33]=[C:32]([NH2:34])[S:31][CH:30]=3)=[N:26]\[O:27][CH3:28])=[O:24])[C:20](=[O:21])[N:17]2[C:16]=1[C:37]([OH:39])=[O:38]>CN(C)C(=O)C.CO>[CH3:12][O:13][CH2:14][C:15]1[CH2:36][S:35][C@@H:18]2[C@H:19]([NH:22][C:23](/[C:25](/[C:29]3[N:33]=[C:32]([NH2:34])[S:31][CH:30]=3)=[N:26]\[O:27][CH3:28])=[O:24])[C:20](=[O:21])[N:17]2[C:16]=1[C:37]([O-:39])=[O:38].[Na+:11]

Participants

5

Reactant 2

HCID 6335986CefpodoximeHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 23669317cefpodoxime sodiumYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

2.03 g of sodium 2-ethylhexanoate was dissolved in a mixture of 12.5 ml of N,N-dimethylacetamide and 50 ml of methanol, 5.0 g of cefpodoxime (7-[2-(2-amino-4-thiazolyl)-(Z)-2-(methoxyimino)acetamido]-3-methoxymethyl -3-cephem-4-carboxylic acid) was added thereto, and the mixture was stirred at room temperature for 30 minutes. Then, methanol was removed under a reduced pressure and 50 ml of acetone was added thereto. The solution was stirred for 30 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 4.98 g of pale yellow cefpodoxime sodium salt (yield: 95%).

Workup

  1. additionwas added
  2. customThen, methanol was removed under a reduced pressure and 50 ml of acetone
  3. additionwas added
  4. stirringThe solution was stirred for 30 minutes
  5. filtrationfiltered
  6. washThe filtered solid was washed with 50 ml of acetone
  7. dry with materialwith 30 ml of isopropyl ether, and vacuum-dried at room temperature

Sources & evidence

ORD record
ord-f6003448ddb3495688256b19219723b7
Source dataset
uspto-grants-2003_10
Patent number
US06639068B1

Reaction notes

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