Methanol → HCID 69157458, compound

HRID 750309Notes

Reaction equation

HRID 750309 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([N:32]3[CH2:37][CH2:36][CH:35]([C:38]([O:40]CC)=[O:39])[CH2:34][CH2:33]3)=[O:31])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].CO.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([N:32]3[CH2:33][CH2:34][CH:35]([C:38]([OH:40])=[O:39])[CH2:36][CH2:37]3)=[O:31])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 69157484HCID 69157484, compound

Product 1

HCID 69157458HCID 69157458, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-bromo-2-[4-(4-ethoxycarbonylpiperidine-1-carbonyl)benzyl]-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (290 mg), methanol (5 ml) and tetrahydrofuran (5 ml) was added a solution (0.1 ml) of 8N aqueous sodium hydroxide and the mixture was stirred at room temperature for 12 hrs. The solvent was evaporated under reduced pressure, water was added and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by preparative liquid chromatography to give the title compound (72 mg, 26%).

Workup

  1. customThe solvent was evaporated under reduced pressure, water
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. customdried
  6. additionby adding sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by preparative liquid chromatography

Sources & evidence

ORD record
ord-db6daee55d384d8290502328c9f07c0a
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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