Sodium Acetate → Sodium 3-azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate

HRID 904915Notes

Reaction equation

HRID 904915 reaction equation
[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:27])[C:18]([C:21]3[N:22]=[C:23]([NH2:26])[S:24][CH:25]=3)=[N:19][OH:20])[C:14](=[O:28])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])=[N+:2]=[N-:3].C([O-])(=O)C.[Na+:33]>CO>[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:27])[C:18]([C:21]3[N:22]=[C:23]([NH2:26])[S:24][CH:25]=3)=[N:19][OH:20])[C:14](=[O:28])[N:9]2[C:10]=1[C:11]([O-:13])=[O:12])=[N+:2]=[N-:3].[Na+:33]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 1317132533-Azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Product 1

HCID 131713254Sodium 3-azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 1 was added to 3 ml of a molar solution of sodium acetate in methanol and the mixture was vacuum filtered to remove slight insolubles. 1 ml of ethanol was added to the filtrate and the mixture was vacuum filtered. 5 ml of ethanol were added to the filtrate and the mixture was vacuum filtered to obtain 0.4 g of the syn isomer of sodium 3-azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate.

Workup

  1. filtrationfiltered
  2. customto remove slight insolubles
  3. addition1 ml of ethanol was added to the filtrate
  4. filtrationfiltered
  5. addition5 ml of ethanol were added to the filtrate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-9207111028fc4494807f308c850d87a3
Source dataset
uspto-grants-1983_12
Patent number
US04420478

Reaction notes

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