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

HRID 848296Notes

Reaction equation

HRID 848296 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-94e2038b3a2d4ad9a71d3371c334c5f9
Source dataset
uspto-grants-1981_10
Patent number
US04294960

Reaction notes

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