Acetic Acid → 2-Methyl-7-(2-cyanoacetamido)-3-cephem-4-carboxylic acid

HRID 851606Notes

Reaction equation

HRID 851606 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:28])[CH:21]([NH:22][C:23](=[O:27])[CH2:24][C:25]#[N:26])[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:28])[CH:21]([NH:22][C:23](=[O:27])[CH2:24][C:25]#[N:26])[C@H:8]2[S:7]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 128339972,2,2-Trichloroethyl 2-methyl-7-(2-cyanoacetamido)-3-cephem-4-carboxylate

Product 1

HCID 128340002-Methyl-7-(2-cyanoacetamido)-3-cephem-4-carboxylic acidYield 105.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

Acetic acid (4 ml) and zinc powder (3 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-cyanoacetamido)-3-cephem-4-carboxylate (3.2 g) in anhydrous dimethylformamide (15 ml), and the mixture was stirred for 1 hour at the same temperature. After the reaction, ethyl acetate (100 ml) was added to the reaction mixture. The insoluble material was filtered off, and the filtrate was washed with 5% hydrochloric acid saturated with sodium chloride, and then extracted with a saturated sodium bicarbonate aqueous solution. The extract was acidified with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. After the solvent was distilled off, the crystalline residue was recrystallized from a mixture of ethyl acetate and benzene to give 2-methyl-7-(2-cyanoacetamido)-3-cephem-4-carboxylic acid (2.3 g), mp 162° to 166° 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% hydrochloric acid saturated with sodium chloride
  5. extractionextracted with a saturated sodium bicarbonate aqueous solution
  6. extractionextracted with ethyl acetate
  7. washThe extract 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 crystalline residue was recrystallized from a mixture of ethyl acetate and benzene

Sources & evidence

ORD record
ord-325116331f7f4c7b8026d4959c550760
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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