Sodium Chloride → HCID 86753074, compound

HRID 2392984Notes

Reaction equation

HRID 2392984 reaction equation
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:12]([NH:22][C@H:23]([C:28]([OH:30])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[NH2:22][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:2][CH:3]=[CH:4][CH:5]=2)[N:10]=1.[C:12]([NH:22][C@H:23]([C:28]([OH:30])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

9

Reactant 6

HCID 5234Sodium ChlorideHCID 113598-AminoquinolineHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86753074HCID 86753074, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 8-aminoquinoline (1 g, 6.9 mmol) and N-CBZ-L-leucine (2.2 g, 8.3 mmol) in dry methylene chloride (35 mL) was mixed with 1-hydroxybenzotriazole (1.1 g, 8.3 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.6 g, 8.3 mmol) . The reaction mixture was stirred overnight at room temperature and then worked up with saturated sodium chloride, saturated sodium bicarbonate, and water. The organic layer was dried with magnesium sulfate. Following solvent removal, product was purified by column chromatography on silica gel eluted with hexane-ethyl acetate (4:1) to give pure CBZ-L-leucine aminoquinoline. It was deprotected by treating it with hydrogen gas and 10% palladium on carbon in ethyl acetate to give pure 8-(L)-leucylaminoquinoline (60% yield).

Workup

  1. dry with materialThe organic layer was dried with magnesium sulfate
  2. customFollowing solvent removal, product
  3. customwas purified by column chromatography on silica gel
  4. washeluted with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-13890a10d233463d9c84479ce2caeaf1
Source dataset
uspto-grants-1998_09
Patent number
US05804400

Reaction notes

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