Hydrochloric Acid → HCID 68828932, compound

HRID 1986492Notes

Reaction equation

HRID 1986492 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:37][CH:38]([CH3:40])[CH3:39])=[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][CH2:31][C:32]([O:34]CC)=[O:33])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)C.[OH-].[Na+].Cl>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:37][CH:38]([CH3:40])[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][CH2:31][C:32]([OH:34])=[O:33])=[CH:15][CH:14]=2)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 68830880HCID 68830880, compound

Product 1

HCID 68828932HCID 68828932, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-{[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}pentanoate (1.6 g, 2.9 mmol) in tetrahydrofuran (10 ml)-ethanol (10 ml) was added 2N aqueous sodium hydroxide solution (3 ml), and the mixture was stirred at room temperature for 5 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 5-{[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}pentanoic acid (1.3 g, yield 87%) 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-63d924bd23d74291a8d1b3a1bef15fa8
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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