Acetic Acid → HCID 12834083, compound

HRID 1764031Notes

Reaction equation

HRID 1764031 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:33])[CH:21]([NH:22][C:23](=[O:32])[CH2:24][O:25][C:26]3[S:27][C:28]([CH3:31])=[N:29][N:30]=3)[C@H:8]2[S:7]1>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:33])[CH:21]([NH:22][C:23](=[O:32])[CH2:24][O:25][C:26]3[S:27][C:28]([CH3:31])=[N:29][N:30]=3)[C@H:8]2[S:7]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70527146HCID 70527146, compound

Product 1

HCID 12834083HCID 12834083, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

Acetic acid (8 ml) and zinc powder (6 g) were added under ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-[2-(5-methyl-1,3,4-thiadiazol-2-yloxy)acetamido]-3-cephem-4-carboxylate (6.60 g) in anhydrous dimethylformamide (40 ml), and the mixture was stirred for 1.5 hours. After the reaction, zinc powder was filtered and washed with dimethylformamide. The filtrate and the washings were combined, and the combined solution was poured into an ice-cooled mixture of ethyl acetate and 2 to 3% hydrochloric acid, and then extracted. The extract was extracted with a sodium bicarbonate aqueous solution and the aqueous solution was acidified with hydrochloric acid, and then extracted with ethyl acetate. The aqueous layer was saturated with sodium chloride, and then extracted, four times with ethylacetate (80 ml), after which the both ethyl acetate extract was combined. After the combined extracted was dried over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was crystallized by adding ether to give dimethylformamide adduct of 2-methyl-7-[2-(5 -methyl-1,3,4-thiadiazol-2-yloxy)acetamido]-3-cephem-4-carboxylic acid (2.0 g), mp 113° to 116° C.

Workup

  1. filtrationwas filtered
  2. washwashed with dimethylformamide
  3. additionthe combined solution was poured into an ice-
  4. temperaturecooled
  5. additionmixture of ethyl acetate and 2 to 3% hydrochloric acid
  6. extractionextracted
  7. extractionThe extract was extracted with a sodium bicarbonate aqueous solution
  8. extractionextracted with ethyl acetate
  9. extractionextracted
  10. extractionfour times with ethylacetate (80 ml), after which the both ethyl acetate extract
  11. extractionAfter the combined extracted
  12. dry with materialwas dried over magnesium sulfate
  13. distillationthe solvent was distilled off under reduced pressure
  14. customThe residue was crystallized
  15. additionby adding ether

Sources & evidence

ORD record
ord-d779592f9a5348b381b78ce6d6e01d52
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

Loading…