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Formate → Sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylate

HRID 27969
Notes
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Reaction equation

HRID 27969 reaction equation
C([O-])=O.[C:4]([O:7][CH2:8][C:9]1[CH2:10][S:11][C@@H:12]2[CH:19]([NH:20][C:21](=[O:32])[C:22]([C:26]3[N:27]=[C:28]([NH2:31])[S:29][CH:30]=3)=[N:23][O:24][CH3:25])[C:18](=[O:33])[N:13]2[C:14]=1[C:15]([OH:17])=[O:16])(=[O:6])[CH3:5].C([O-])(=O)C.[Na+:38]>O.C(O)C>[C:4]([O:7][CH2:8][C:9]1[CH2:10][S:11][C@@H:12]2[CH:19]([NH:20][C:21](=[O:32])[C:22]([C:26]3[N:27]=[C:28]([NH2:31])[S:29][CH:30]=3)=[N:23][O:24][CH3:25])[C:18](=[O:33])[N:13]2[C:14]=1[C:15]([O-:17])=[O:16])(=[O:6])[CH3:5].[Na+:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 283FormateHCID 517045Sodium AcetateHCID 1317115033-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Product 1

HCID 131711736Sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylateYield 0.95%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

10 g of the formate solvate of the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid (described in Belgium Pat. No. 850,662) were added at room temperature to a solution of 3.5 g of sodium acetate in 5 ml of water and 300 ml of ethanol and when dissolution was complete, the mixture was filtered. The filtrate was added dropwise over one hour with stirring at room temperature to 160 ml of absolute ethanol and the resulting mixture was stirred at room temperature for 3 hours and at 0° C. for 16 hours. The mixture was vacuum filtered and the crystals were washed with ethanol and dried under reduced pressure to obtain 7.75 g of the crystalline D form of the syn isomer of sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylate containing 0.95% of water.

Workup

  1. filtrationthe mixture was filtered
  2. additionThe filtrate was added dropwise over one hour
  3. stirringthe resulting mixture was stirred at room temperature for 3 hours and at 0° C. for 16 hours
  4. filtrationfiltered
  5. washthe crystals were washed with ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-39112f5f0b064c6794dc4d0d27cfd8e6
Source dataset
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04224371

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes