Acetic Acid → 2-Methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid

HRID 851603Notes

Reaction equation

HRID 851603 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:31])[CH:21]([NH:22][C:23](=[O:30])[CH2:24][C:25]3[S:26][CH:27]=[CH:28][CH:29]=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:31])[CH:21]([NH:22][C:23](=[O:30])[CH2:24][C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[C@H:8]2[S:7]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 12833985HCID 12833985, compound

Product 1

HCID 128339882-Methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acidYield 92.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

Acetic acid (3 ml) and zinc powder (2.4 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylate (1.8 g) in anhydrous dimethyl-formamide (10 ml), and the mixture was stirred for 1 hour at the same temperature. After the reaction, zinc powder was filtered off, and the filtrate was extracted by pouring into a mixture of 5% hydrochloric acid (50 ml) and ethyl acetate (40 ml). The ethyl acetate layer was washed with water and dried. After the solvent was distilled off, the residue was dissolved in ether and allowed to stand, after which the precipitating crystals were collected by filtration and dried to give 2-methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid (1.2 g), mp 175° C. (dec.).

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. filtrationwas filtered off
  3. extractionthe filtrate was extracted
  4. additionby pouring into a mixture of 5% hydrochloric acid (50 ml) and ethyl acetate (40 ml)
  5. washThe ethyl acetate layer was washed with water
  6. customdried
  7. distillationAfter the solvent was distilled off
  8. dissolutionthe residue was dissolved in ether
  9. filtrationafter which the precipitating crystals were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-821c97ede22c4ff9876a5db64a7f230a
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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