Trifluoroacetic acid → HCID 88818598, compound

HRID 596841Notes

Reaction equation

HRID 596841 reaction equation
[CH:1]([O:3][CH:4]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:5]([NH:7][CH:8]1[C:34](=[O:35])[N:10]2[C:11]([C:18]([O:20]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:19])=[C:12]([C:15](=[O:17])[CH3:16])[CH2:13][S:14][C@H:9]12)=[O:6])=[O:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.CCCCCCC>CC(C)=O>[CH:1]([O:3][CH:4]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:5]([NH:7][CH:8]1[C:34](=[O:35])[N:10]2[C:11]([C:18]([OH:20])=[O:19])=[C:12]([C:15](=[O:17])[CH3:16])[CH2:13][S:14][C@H:9]12)=[O:6])=[O:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 8900HeptaneHCID 131710675HCID 131710675, compound

Product 1

HCID 88818598HCID 88818598, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
5 °C

Procedure

To a cooled (5° C.), stirred slurry of 0.194 g. of benzhydryl 7-(2-formyloxy-2-phenylacetamido)-3-acetyl-3-cephem-4-carboxylate in 10 ml. of anisole was added 1 ml. of cold trifluoroacetic acid. After allowing the reaction mixture to stir with cooling for 15 minutes, 30 ml. of n-heptane was added and the resulting solution was evaporated in vacuo to a low volume. An additional 30 ml. of n-heptane was added, and the resulting solution was stirred with cooling in an ice bath for 5 minutes. The solid obtained by filtration of the n-heptane solution was dissolved in acetone, the acetone solution was filtered, and the filtrate was evaporated in vacuo to a low volume. The residue was transferred with the aid of cold ethyl acetate to a separatory funnel where the resulting 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 organic layer was separated, washed twice with brine, and dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided 0.136 g. (99.3 percent) of the title product as a white froth which failed to crystallize from aceonte/hexane or chloroform/hexane:

Workup

  1. stirringto stir
  2. temperaturewith cooling for 15 minutes
  3. customthe resulting solution was evaporated in vacuo to a low volume
  4. additionof n-heptane was added
  5. stirringthe resulting solution was stirred
  6. temperaturewith cooling in an ice bath for 5 minutes
  7. customThe solid obtained by filtration of the n-heptane solution
  8. filtrationthe acetone solution was filtered
  9. customthe filtrate was evaporated in vacuo to a low volume
  10. customThe residue was transferred with the aid of cold ethyl acetate to a separatory funnel
  11. extractionwhere the resulting ethyl acetate solution was extracted twice with cold aqueous sodium bicarbonate solution
  12. customThe organic layer was separated
  13. washwashed twice with brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. customEvaporation in vacuo to dryness
  16. customprovided 0.136 g

Sources & evidence

ORD record
ord-478bdd4a2b4a44b9ad7bf3e71ed74904
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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