Acetic Acid → HCID 12833982, compound

HRID 1764026Notes

Reaction equation

HRID 1764026 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][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=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][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[C@H:8]2[S:7]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 12833979HCID 12833979, compound

Product 1

HCID 12833982HCID 12833982, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

Acetic acid (4.1 ml) and zinc powder (3.4 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-[2-(3-chlorophenyl)acetamido]-3-cephem-4-carboxylate (2.6 g) in anhydrous dimethylformamide (30 ml), and the mixture was stirred for 1.5 hours at the same temperature. After the reaction, zinc powder was filtered off, and the filtrate was poured into a mixture of 5% hydrochloric acid (150 ml) and ethyl acetate (75 ml), and then extracted. The extract was washed with water and dried. After the solvent was distilled off, the residue was crystallized by adding acetonitrile. The crystals were collected by filtration, washed with ether and dried to give colorless crystals of 2-methyl-7-[2-(3-chlorophenyl)acetamido]-3-cephem-4-carboxylic acid (1.4 g), mp 173° to 174° C. (dec.).

Workup

  1. stirringthe mixture was stirred for 1.5 hours at the same temperature
  2. filtrationwas filtered off
  3. additionthe filtrate was poured into a mixture of 5% hydrochloric acid (150 ml) and ethyl acetate (75 ml)
  4. extractionextracted
  5. washThe extract was washed with water
  6. customdried
  7. distillationAfter the solvent was distilled off
  8. customthe residue was crystallized
  9. additionby adding acetonitrile
  10. filtrationThe crystals were collected by filtration
  11. washwashed with ether
  12. customdried

Sources & evidence

ORD record
ord-c7b394296f5b449b944c4101a7d9274c
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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