Sodium Acetate Trihydrate → 7-{2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido}-2,3-dimethyl-3-cephem-4-carboxylic acid

HRID 1074744Notes

Reaction equation

HRID 1074744 reaction equation
FC(F)(F)C([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:29][O:30][CH3:31])[C:12]([NH:14][CH:15]2[C:27](=[O:28])[N:17]3[C:18]([C:24]([OH:26])=[O:25])=[C:19]([CH3:23])[CH:20]([CH3:22])[S:21][C@H:16]23)=[O:13])[N:10]=1)=O.O.O.O.C([O-])(=O)C.[Na+]>>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:29][O:30][CH3:31])[C:12]([NH:14][CH:15]2[C:27](=[O:28])[N:17]3[C:18]([C:24]([OH:26])=[O:25])=[C:19]([CH3:23])[CH:20]([CH3:22])[S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

3

Reactant 2

HCID 23665404Sodium Acetate TrihydrateHCID 1317124377-[2-{2-(2,2,2-Trifluoroacetamido)-4-thiazolyl}--2-methoxyiminoacetamido]-2,3-dimethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317124387-{2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido}-2,3-dimethyl-3-cephem-4-carboxylic acidYield 22.9%

Procedure

7-[2-{2-(2,2,2-Trifluoroacetamido)-4-thiazolyl}-2-methoxyiminoacetamido]-2,3-dimethyl-3-cephem-4-carboxylic acid (syn isomer, 0.86 g.) was dissolved in an aqueous solution (9 ml.) containing sodium acetate trihydrate (2.3 g.), and the solution was stirred at room temperature for 19 hours. After removing the insoluble substance from the resultant mixture by filtration, the filtrate was adjusted to around pH 2.5 with 10% hydrochloric acid under ice-cooling. The precipitates were collected by filtration, washed with water and dried to give 7-{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido}-2,3-dimethyl-3-cephem-4-carboxylic acid (syn isomer, 0.16 g.).

Workup

  1. customAfter removing the insoluble substance from the resultant mixture
  2. filtrationby filtration
  3. temperaturecooling
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ef6e8376f60f4f90a7a70eacc2c45559
Source dataset
uspto-grants-1983_07
Patent number
US04393059

Reaction notes

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