Methanol → HCID 68831781, compound

HRID 1986423Notes

Reaction equation

HRID 1986423 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:30][CH:31]([CH3:33])[CH3:32])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][C:16]([C:26]([O:28]C)=[O:27])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:30][CH:31]([CH3:33])[CH3:32])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[CH:17][C:16]([C:26]([OH:28])=[O:27])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68829895HCID 68829895, compound

Product 1

HCID 68831781HCID 68831781, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-phenylquinoline-6-carboxylate (0.58 g, 1.3 mmol) in tetrahydrofuran (6 ml)-methanol (6 ml) was added 1N aqueous sodium hydroxide solution (3 ml), and the mixture was stirred at 50° C. for 2 hrs. The reaction mixture was partitioned between tetrahydrofuran (50 ml)-ethyl acetate (50 ml) and 0.1N hydrochloric acid (100 ml) and the aqueous layer was extracted twice with tetrahydrofuran (25 ml)-ethyl acetate (25 ml). The organic layers were combined, washed with saturated brine (50 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was crystallized from diisopropyl ether-ethyl acetate to give 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-phenylquinoline-6-carboxylic acid (0.56 g, 99%) as colorless crystals.

Workup

  1. customThe reaction mixture was partitioned between tetrahydrofuran (50 ml)-ethyl acetate (50 ml) and 0.1N hydrochloric acid (100 ml)
  2. extractionthe aqueous layer was extracted twice with tetrahydrofuran (25 ml)-ethyl acetate (25 ml)
  3. washwashed with saturated brine (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was crystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-18d1207964dc4489a4cc83622f5529d4
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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