HCID 70561409, compound → 7-[2-(2-Thienyl)acetamido]-3-fluoro-3-cephem-4-carboxylic acid

HRID 1657742Notes

Reaction equation

HRID 1657742 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20]CC3C=CC([N+]([O-])=O)=CC=3)=[O:19])=[C:14]([F:17])[CH2:15][S:16][C@H:11]12)=[O:8]>[Pd].CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([OH:20])=[O:19])=[C:14]([F:17])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 1

HCID 70561409HCID 70561409, compound

Product 1

HCID 705600817-[2-(2-Thienyl)acetamido]-3-fluoro-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 110 ml. of methanol and 83 mg. of pre-reduced 5 percent palladium on carbon were added 83 mg. of p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-fluoro-3-cephem-4-carboxylate. The mixture was hydrogenated at 53 psig. for one hour. The resulting mixture was filtered, the filtered catalyst was washed with methanol, and the methanol washings were added to the filtrate. The filtrate was then evaporated in vacuo. The residue was dissolved in ethyl acetate, and the ethyl acetate solution was extracted with dilute aqueous sodium bicarbonate. The sodium bicarbonate solution was washed with ethyl acetate, layered with ethyl acetate, and dilute aqueous HCl was added. The layered ethyl acetate was separated and evaporated to recover 7-[2-(2-thienyl)acetamido]-3-fluoro-3-cephem-4-carboxylic acid, shown by bioautogram to be biologically active.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe filtered catalyst was washed with methanol
  3. additionthe methanol washings were added to the filtrate
  4. customThe filtrate was then evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. extractionthe ethyl acetate solution was extracted with dilute aqueous sodium bicarbonate
  7. washThe sodium bicarbonate solution was washed with ethyl acetate
  8. additionwas added
  9. customThe layered ethyl acetate was separated
  10. customevaporated
  11. customto recover 7-[2-(2-thienyl)acetamido]-3-fluoro-3-cephem-4-carboxylic acid

Sources & evidence

ORD record
ord-649928655c7b426d80f6986b184645ac
Source dataset
uspto-grants-1976_06
Patent number
US03962227

Reaction notes

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