Hydrochloric Acid → 5-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoic aicd

HRID 585376Notes

Reaction equation

HRID 585376 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([N:18]2[C:27]3[C:22](=[CH:23][C:24]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[CH:25][CH:26]=3)[CH2:21][CH2:20][CH2:19]2)[CH2:10][CH:9]1[CH3:38])=[O:7].C(O)C.O.[OH-].[Li+].Cl>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([N:18]2[C:27]3[C:22](=[CH:23][C:24]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:25][CH:26]=3)[CH2:21][CH2:20][CH2:19]2)[CH2:10][CH:9]1[CH3:38])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 22339324Ethyl 5-[[1-[1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoate

Product 1

HCID 223392615-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoic aicdYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-[[1-[1-(3,4-dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoate (100 mg, 0.17 mmol) prepared in Example 94 was dissolved in THF (3 ml), ethanol (2 ml) and water (2 ml), to which lithium hydroxide monohydrate (21 mg, 0.51 mmol) was then added and stirred at room temperature for 3 hours. The reaction mixture was neutralized with 1N hydrochloric acid and then extracted with ethyl acetate. After the organic layer was dried and concentrated, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=4/1) to give the titled compound (33 mg, yield: 35%) as a colorless oil. (cis:trans=1:1.5)

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter the organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0cb759a2f55543b9a4643d503acee821
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Reaction notes

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