Acetic Acid → HCID 70526346, compound

HRID 1764030Notes

Reaction equation

HRID 1764030 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:39])[CH:21]([NH:22][C:23](=[O:38])[CH:24]([C:33]3[S:34][CH:35]=[CH:36][CH:37]=3)[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[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:39])[CH:21]([NH:22][C:23](=[O:38])[CH:24]([C:33]3[S:34][CH:35]=[CH:36][CH:37]=3)[NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[C@H:8]2[S:7]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70527417HCID 70527417, compound

Product 1

HCID 70526346HCID 70526346, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

Acetic acid (1.6 ml) and zinc powder (1.2 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-[N-tert.-butoxycarbonyl-2-(2-thienyl)glycyl]amino-3-cephem-4-carboxylate (1.52 g) in anhydrous dimethylformamide (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 poured into an ice-cooled mixture of 2 to 3% hydrochloric acid and ethyl acetate and then extracted. The extract was washed with water, extracted with a sodium bicarbonate aqueous solution, after which the aqueous layer was acidified by adding 5% sulfuric acid and ethyl acetate and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was pulverized by adding isopropyl ether, collected by filtration and dried to give amorphous 2-methyl-7-[N-tert.-butoxycarbonyl-2-(2-thienyl)glycyl]amino-3-cephem-4-carboxylic acid (0.7 g).

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. filtrationwas filtered off
  3. additionthe filtrate was poured into an ice-
  4. temperaturecooled
  5. additionmixture of 2 to 3% hydrochloric acid and ethyl acetate
  6. extractionextracted
  7. washThe extract was washed with water
  8. extractionextracted with a sodium bicarbonate aqueous solution
  9. additionby adding 5% sulfuric acid and ethyl acetate
  10. extractionextracted with ethyl acetate
  11. washThe extract was washed with water
  12. dry with materialdried over magnesium sulfate
  13. distillationby distilling off the solvent under reduced pressure
  14. additionby adding isopropyl ether
  15. filtrationcollected by filtration
  16. customdried

Sources & evidence

ORD record
ord-02328af1ae7e4b6399cd77ce6e6f97e4
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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