Sodium Hydroxide → Sodium 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 848309Notes

Reaction equation

HRID 848309 reaction equation
[OH-].[Na+:2].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH3:27])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1>O>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH3:27])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([O-:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1.[Na+:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1317124447-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 131712445Sodium 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4N Aqueous solution of sodium hydroxide was carefully added dropwise to a stirred suspension of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 52 g.) in water (100 ml.) below 5° C. to make a solution of pH 7.0 to 7.5. After filtration and washing, the combined filtrate and the washings (200 ml.) was added dropwise to ethanol (2 l.) under stirring over 30 minutes, and stirred at room temperature for 15 minutes and then at 5° to 10° C. for an hour. The precipitates were collected by filtration, washed with ethanol (200 ml.) and dried in vacuo at 30° C. to give amorphous sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 46.3 g.).

Workup

  1. filtrationAfter filtration
  2. washwashing
  3. additionthe combined filtrate and the washings (200 ml.) was added dropwise to ethanol (2 l.)
  4. stirringstirred at room temperature for 15 minutes
  5. waitat 5° to 10° C. for an hour
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with ethanol (200 ml.)
  8. customdried in vacuo at 30° C.

Sources & evidence

ORD record
ord-8c57cadf452241cd90f83f7c8236086c
Source dataset
uspto-grants-1981_10
Patent number
US04294960

Reaction notes

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