Trifluoroacetic acid → HCID 70635414, compound

HRID 596833Notes

Reaction equation

HRID 596833 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:36](=[O:37])[N:12]2[C:13]([C:20]([O:22]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:21])=[C:14]([C:17](=[O:19])[CH3:18])[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:36](=[O:37])[N:12]2[C:13]([C:20]([OH:22])=[O:21])=[C:14]([C:17](=[O:19])[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 70636138HCID 70636138, compound

Product 1

HCID 70635414HCID 70635414, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
5 °C

Procedure

To a cooled (5° C.) stirred slurry of 0.100 g. of benzhydryl 7-(2-thienylacetamido)-3-acetyl-3-cephem-4-carboxylate in 1 ml. of anisole was added 1 ml. of cold trifluoroacetic acid. The ester immediately dissolved. The resulting colorless solution was stirred with cooling for 20 minutes after which time approximately 40 ml. of n-heptane was added. The resulting solution was evaporated in vacuo to a low volume causing the precipitation of a white solid. The solid was filtered from the mixture and subsequently dissolved in acetone. The acetone solution was filtered and then evaporated in vacuo to dryness. The residue was dissolved in ethyl acetate, and the resulting solution was extracted three times with cold sodium bicarbonate solution. The aqueous extracts were combined, layered with ethyl acetate and acidified with 1N.HCl. The ethyl acetate layer was separated, washed with brine and dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness gave 0.067 g. of the title product as a pale yellow solid which failed to crystallize from methylene chloride-hexane:

Workup

  1. stirringThe resulting colorless solution was stirred
  2. temperaturewith cooling for 20 minutes after which time approximately 40 ml
  3. customThe resulting solution was evaporated in vacuo to a low volume
  4. customthe precipitation of a white solid
  5. filtrationThe solid was filtered from the mixture
  6. dissolutionsubsequently dissolved in acetone
  7. filtrationThe acetone solution was filtered
  8. customevaporated in vacuo to dryness
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. extractionthe resulting solution was extracted three times with cold sodium bicarbonate solution
  11. customThe ethyl acetate layer was separated
  12. washwashed with brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. customEvaporation in vacuo to dryness
  15. customgave 0.067 g

Sources & evidence

ORD record
ord-0aefca99df914c5f97220871b87291f2
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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