Reaction #969877

Reaction equation

6-aminoquinoline

1-hydroxibenzotriazol

Z-Val-Pro-OH

N,N′-diisopropylcarbodiimide

→

Z-Val-Pro 6-aminoquinoline

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherwas continued until the complete disappearance of the starting material (overnight)
2. 2
   OtherThen, the solvent was evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   Washwashed with citric acid (10%), NaHCO3 (10%) and brine
5. 5
   DryingThe organic layer was dried (Na2SO4)
6. 6
   Otherevaporated
7. 7
   Otherleaving a residue that
8. 8
   Otherwas purified by CCTLC on the chromatotron with hexane/ethyl acetate (1:4)
9. 9
   Otherto yield H (20
10. 10
    Otheryield

Procedure

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

Source