Acetic Acid → 2-Methyl-7-[2-(1,3,4-thiadiazol-2-ylthio)-acetamido]-3-cephem-4-carboxylic acid

HRID 851608Notes

Reaction equation

HRID 851608 reaction equation
C(O)(=O)C.[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([O:14]CC(Cl)(Cl)Cl)=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][S:25][C:26]3[S:27][CH:28]=[N:29][N:30]=3)[C@H:8]2[S:7]1.C(OCC)(=O)C>CN(C)C=O.[Zn]>[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][S:25][C:26]3[S:27][CH:28]=[N:29][N:30]=3)[C@H:8]2[S:7]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 128340152,2,2-Trichloroethyl 2-methyl-7-[2-(1,3,4-thiadiazol-2-yithio)acetamido]-3-cephem-4-carboxylate

Product 1

HCID 128340182-Methyl-7-[2-(1,3,4-thiadiazol-2-ylthio)-acetamido]-3-cephem-4-carboxylic acidYield 43.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

Acetic acid (8 ml) and zinc powder (6 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-[2-(1,3,4-thiadiazol-2-ylthio)-acetamido]-3-cephem-4-carboxylate (4.65 g) in anhydrous dimethylformamide (30 ml), and the mixture was stirred for 1 hour at the same temperature. After the reaction, ethyl acetate (150 ml) was added to the reaction mixture. The insoluble material was filtered off, and the filtrate was washed with 5% hydrochloride acid saturated with sodium chloride, and then extracted with a sodium bicarbonate aqueous solution. The extract was acidified with 10% hydrochloric acid and extracted with ethyl acetate, after which the ethyl acetate layer was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. After the solvent was distilled off, the residue was recrystallized from a mixture of ethyl acetate and benzene to give 2-methyl-7-[2-(1,3,4-thiadiazol-2-ylthio)-acetamido]-3-cephem-4-carboxylic acid (1.5 g), mp 197° to 199° C.

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. additionwas added to the reaction mixture
  3. filtrationThe insoluble material was filtered off
  4. washthe filtrate was washed with 5% hydrochloride acid saturated with sodium chloride
  5. extractionextracted with a sodium bicarbonate aqueous solution
  6. extractionextracted with ethyl acetate
  7. washafter which the ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over magnesium sulfate
  9. distillationAfter the solvent was distilled off
  10. customthe residue was recrystallized from a mixture of ethyl acetate and benzene

Sources & evidence

ORD record
ord-cd7e7608428c487ca0b4cb751d6e198d
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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