Hydrochloric Acid → HCID 68828184, compound

HRID 1986488Notes

Reaction equation

HRID 1986488 reaction equation
[C:1]([O:5][C:6]([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][CH:28]([CH2:34][CH3:35])C(OCC)=O)=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:40]([OH:42])C.[OH-:43].[Na+].Cl>O1CCCC1>[C:1]([O:5][C:6]([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][CH2:34][CH2:35][C:40]([OH:42])=[O:43])=[CH:15][CH:14]=2)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86605658HCID 86605658, compound

Product 1

HCID 68828184HCID 68828184, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl {[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}butanoate (1.8 g, 3.4 mmol) in tetrahydrofuran (20 ml)-ethanol (20 ml) was added 2N aqueous sodium hydroxide solution (4 ml), and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was acidified with 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was crystallized from diisopropyl ether to give 4-{[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}butanoic acid (1.3 g, yield 76%) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-1e83006d95ff421c936beae95da72d9c
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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