Trifluoroacetic acid → HCID 70635670, compound

HRID 596845Notes

Reaction equation

HRID 596845 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:37](=[O:38])[N:12]2[C:13]([C:21]([O:23]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:22])=[C:14]([C:17](=[O:20])[CH2:18][CH3:19])[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:37](=[O:38])[N:12]2[C:13]([C:21]([OH:23])=[O:22])=[C:14]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131710677HCID 131710677, compound

Product 1

HCID 70635670HCID 70635670, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
5 °C

Procedure

To a cooled (5° C.), stirred slurry of 0.168 g. of benzhydryl 7-(2-thienylacetamido)-3-propionyl-3-cephem-4-carboxylate in 2 ml. of anisole was added 1 ml. of cold trifluoroacetic acid. The reaction mixture was allowed to stir with cooling for 20 minutes after which time 30 ml. of n-heptane was added. After the resulting solution was evaporated in vacuo to a low volume to remove excess trifluoroacetic acid, an additional 30 ml. of n-heptane was added. After stirring the reaction mixture in an ice bath for five minutes the mixture was filtered. The solid was dissolved in acetone, and the acetone solution was filtered. The filtrate was evaporated to low volume and subsequently transferred to a separatory funnel with the aid of cold ethyl acetate. 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 organic layer was separated and washed twice with brine and dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided 0.108 g. (92 percent) of the title product as a white solid:

Workup

  1. stirringto stir
  2. temperaturewith cooling for 20 minutes after which time 30 ml
  3. customAfter the resulting solution was evaporated in vacuo to a low volume
  4. customto remove excess trifluoroacetic acid
  5. additionof n-heptane was added
  6. stirringAfter stirring the reaction mixture in an ice bath for five minutes the mixture
  7. filtrationwas filtered
  8. dissolutionThe solid was dissolved in acetone
  9. filtrationthe acetone solution was filtered
  10. customThe filtrate was evaporated to low volume
  11. customsubsequently transferred to a separatory funnel with the aid of cold ethyl acetate
  12. extractionThe ethyl acetate solution was extracted twice with cold aqueous sodium bicarbonate solution
  13. customThe organic layer was separated
  14. washwashed twice with brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. customEvaporation in vacuo to dryness
  17. customprovided 0.108 g

Sources & evidence

ORD record
ord-d7f3da37a766434f847e4e8a885f2ae0
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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