Hydrochloric Acid → HCID 68828564, compound

HRID 1986487Notes

Reaction equation

HRID 1986487 reaction equation
C(OC([NH:8][CH2:9][C:10]1[C:11]([CH2:36][CH:37]([CH3:39])[CH3:38])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:15][CH:14]=2)=O)(C)(C)C.Cl>C(OCC)(=O)C>[NH2:8][CH2:9][C:10]1[C:11]([CH2:36][CH:37]([CH3:38])[CH3:39])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)=[CH:17][C:16]([O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:15][CH:14]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68833731HCID 68833731, compound

Product 1

HCID 68828564HCID 68828564, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of ethyl 4-{[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}butanoate (0.2 g, 0.37 mmol) in ethyl acetate (10 ml) was added 4N solution of hydrogen chloride in ethyl acetate (10 ml), and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was concentrated under reduced pressure and saturated aqueous sodium hydrogen carbonate was added to neutralize the residue. The obtained mixture was extracted with ethyl acetate and the extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give ethyl 4-{[3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)-6-quinolinyl]oxy}butanoate (0.12 g) as an oil. The oil and p-toluenesulfonic acid monohydrate (57 mg, 0.25 mmol) were dissolved in ethanol (10 ml) and the mixture was concentrated under reduced pressure. The residue was crystallized from diethyl ether to give the title compound (0.11 g, yield 50%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and saturated aqueous sodium hydrogen carbonate
  2. additionwas added
  3. extractionThe obtained mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14ab05fd192d4da1be358115256fedca
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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