Reaktion #969877

ord-837f8df55324406d983aa5ce7878dffa

Reaktionsgleichung

Nc1ccc2ncccc2c1
6-aminoquinoline
On1nnc2ccccc21
1-hydroxibenzotriazol
CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C(=O)O
Z-Val-Pro-OH
CC(C)N=C=NC(C)C
N,N′-diisopropylcarbodiimide
CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C(=O)O.Nc1ccc2ncccc2c1
Z-Val-Pro 6-aminoquinoline

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewas continued until the complete disappearance of the starting material (overnight)
  2. 2
    SonstigeThen, the solvent was evaporated
  3. 3
    workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
  4. 4
    Waschenwashed with citric acid (10%), NaHCO3 (10%) and brine
  5. 5
    TrocknenThe organic layer was dried (Na2SO4)
  6. 6
    Sonstigeevaporated
  7. 7
    Sonstigeleaving a residue that
  8. 8
    Sonstigewas purified by CCTLC on the chromatotron with hexane/ethyl acetate (1:4)
  9. 9
    Sonstigeto yield H (20
  10. 10
    Sonstigeyield

Vorschrift

A solution of Z-Val-Pro-OH (217.4 mg, 0.62 mmol) in dichloromethane (1.5 mL), was successively treated at room temperature. with 1-hydroxibenzotriazol (84.3 mg, 0.62 mmol), N,N′-diisopropylcarbodiimide (97.2 μL, 0.62 mmol) and 6-aminoquinoline (75 mg, 0.52 mmol). The stirring was continued until the complete disappearance of the starting material (overnight). Then, the solvent was evaporated, the residue was dissolved in ethyl acetate and washed with citric acid (10%), NaHCO3 (10%) and brine. The organic layer was dried (Na2SO4) and evaporated leaving a residue that was purified by CCTLC on the chromatotron with hexane/ethyl acetate (1:4) to yield H (20 yield

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08236756B2uspto-grants-2012_08