Trifluoroacetic acid → HCID 11131919, compound

HRID 1457063Notes

Reaction equation

HRID 1457063 reaction equation
[CH3:1][N:2]([CH3:24])[CH:3]1[CH2:23][CH2:22][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([NH:14][C:15](OC(C)(C)C)=[O:16])=[CH:10][C:9]=3[C:5]=2[CH2:4]1.FC(F)(F)C(O)=O.[F:32][C:33]1[CH:41]=[CH:40][C:36](C(Cl)=O)=[CH:35][CH:34]=1>>[CH3:1][N:2]([CH3:24])[CH:3]1[CH2:23][CH2:22][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:16])[C:36]4[CH:40]=[CH:41][C:33]([F:32])=[CH:34][CH:35]=4)=[CH:10][C:9]=3[C:5]=2[CH2:4]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 678794-Fluorobenzoyl chlorideHCID 21221611HCID 21221611, compound

Product 1

HCID 11131919HCID 11131919, compoundYield 60.3%

Procedure

A mixture of 0.090 gm (0.273 mMol) of (+)-N,N-dimethyl-8-(tert-butoxycarbonyl)amino-1,2,3,4-tetrahydro-2-dibenzofuranamine and 1 mL of trifluoro-acetic acid was stirred at room temperature for 20 minutes. The excess trifluoroacetic acid was then removed under reduced pressure. The residue was dissolved in 5 mL of tetrahydrofuran and to this solution were added 1.5 mL of triethylamine followed by 0.05 mL (0.42 mMol) of 4-fluorobenzoyl chloride. After stirring for 1 hour the volatiles were removed under reduced pressure. The residue was taken up in 5 mL of dichloromethane and stirred with dilute aqueous sodium carbonate. After stirring for 16 hours the dichloromethane layer was separated and the aqueous layer extracted with fresh dichloromethane. The dichloromethane extracts were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 5% methanol (containing 5% ammonium hydroxide) in chloroform. Fractions containing product were combined and concentrated under reduced pressure. The resulting residue was crystallized from toluene/hexane to provide 0.058 gm (60%) of the title compound as a crystalline solid in two crops.

Workup

  1. customThe excess trifluoroacetic acid was then removed under reduced pressure
  2. dissolutionThe residue was dissolved in 5 mL of tetrahydrofuran and to this solution
  3. additionwere added 1.5 mL of triethylamine
  4. stirringAfter stirring for 1 hour the volatiles
  5. customwere removed under reduced pressure
  6. stirringstirred with dilute aqueous sodium carbonate
  7. stirringAfter stirring for 16 hours the dichloromethane layer
  8. customwas separated
  9. extractionthe aqueous layer extracted with fresh dichloromethane
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. washeluting with 5% methanol (containing 5% ammonium hydroxide) in chloroform
  13. additionFractions containing product
  14. concentrationconcentrated under reduced pressure
  15. customThe resulting residue was crystallized from toluene/hexane

Sources & evidence

ORD record
ord-a6a6c54cac484ba8b4e8c22aba7c3759
Source dataset
uspto-grants-1998_12
Patent number
US05846995

Reaction notes

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