Trifluoroacetic acid → HCID 70635502, compound

HRID 596847Notes

Reaction equation

HRID 596847 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:41](=[O:42])[N:12]2[C:13]([C:25]([O:27]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:26])=[C:14]([C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>CCCCCCC>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:41](=[O:42])[N:12]2[C:13]([C:25]([OH:27])=[O:26])=[C:14]([C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131710679HCID 131710679, compound

Product 1

HCID 70635502HCID 70635502, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
5 °C

Procedure

To a cooled (5° C.), stirred slurry of 0.227 g. of benzhydryl 7-(2-thienylacetamido)-3-benzoyl-3-cephem-4-carboxylate in 2 ml. of anisole was added 1 ml. of cold trifluoroacetic acid. After the reaction mixture was allowed to stir with cooling for 20 minutes, 20 ml. of n-heptane was added, and the resulting solution was evaporated in vacuo to a low volume to remove excess trifluoroacetic acid. An additional 20 ml. of n-heptane was added to the residue and the resulting solution was stirred with cooling for approximately 5 minutes. The white precipitate which formed was filtered from the solution and dissolved in acetone. The acetone solution was filtered and the filtrate evaporated in vacuo to a low volume. The residue was dissolved in cold ethyl acetate and transferred to a separatory funnel. The ethyl acetate solution was extracted twice with cold aqueous sodium bicarbonate solution. The aqueous extracts were combined, layered with cold ethyl acetate and acidified with cold 1N.HCl. The ethyl acetate layer was separated, washed twice with brine, and dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided 0.157 g. (96 percent) of the title acid which crystallized from methylene chloride/hexane. The product exhibited activity against gram-positive and gram-negative organisms at 0.1 mg/ml in a standard disc assay.

Workup

  1. stirringto stir
  2. temperaturewith cooling for 20 minutes
  3. customthe resulting solution was evaporated in vacuo to a low volume
  4. customto remove excess trifluoroacetic acid
  5. additionof n-heptane was added to the residue
  6. stirringthe resulting solution was stirred
  7. temperaturewith cooling for approximately 5 minutes
  8. customThe white precipitate which formed
  9. filtrationwas filtered from the solution
  10. dissolutiondissolved in acetone
  11. filtrationThe acetone solution was filtered
  12. customthe filtrate evaporated in vacuo to a low volume
  13. dissolutionThe residue was dissolved in cold ethyl acetate
  14. customtransferred to a separatory funnel
  15. extractionThe ethyl acetate solution was extracted twice with cold aqueous sodium bicarbonate solution
  16. customThe ethyl acetate layer was separated
  17. washwashed twice with brine
  18. dry with materialdried over anhydrous sodium sulfate
  19. customEvaporation in vacuo to dryness
  20. customprovided 0.157 g
  21. custom(96 percent) of the title acid which crystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-605e7224adba407a9e0e317e2bd05822
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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