6-Aminoquinoline → Z-Val-Pro 6-aminoquinoline

HRID 882695Notes

Reaction equation

HRID 882695 reaction equation
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.[NH2:45][C:46]1[CH:47]=[C:48]2[C:53](=[CH:54][CH:55]=1)[N:52]=[CH:51][CH:50]=[CH:49]2>ClCCl>[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[NH2:45][C:46]1[CH:47]=[C:48]2[C:53](=[CH:54][CH:55]=1)[N:52]=[CH:51][CH:50]=[CH:49]2

Participants

6

Reactant 4

HCID 113736-AminoquinolineHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10783923Z-Val-pro-OH

Product 1

HCID 131729872Z-Val-Pro 6-aminoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

Workup

  1. customwas continued until the complete disappearance of the starting material (overnight)
  2. customThen, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with citric acid (10%), NaHCO3 (10%) and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated
  7. customleaving a residue that
  8. customwas purified by CCTLC on the chromatotron with hexane/ethyl acetate (1:4)
  9. customto yield H (20
  10. customyield

Sources & evidence

ORD record
ord-837f8df55324406d983aa5ce7878dffa
Source dataset
uspto-grants-2012_08
Patent number
US08236756B2

Reaction notes

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