Sodium Hydroxide → HCID 69156808, compound

HRID 750144Notes

Reaction equation

HRID 750144 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](=[O:37])[NH:31][CH2:32][C:33]([O:35]C)=[O:34])=[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].[OH-].[Na+]>CO.O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:30](=[O:37])[NH:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:28][CH:29]=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 2

HCID 14798Sodium HydroxideHCID 69157439HCID 69157439, compound

Product 1

HCID 69156808HCID 69156808, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 6-bromo-2-[4-(methoxycarbonylmethylcarbamoyl)benzyl]-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (100 mg) in methanol (3 ml) and tetrahydrofuran (3 ml) was added 8N aqueous sodium hydroxide solution (0.05 ml), 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 dichloromethane. The extract was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure, and methanol was added to the obtained residue. The mixture was crystallized to give the title compound (15 mg, 15%).

Workup

  1. customThe solvent was evaporated under reduced pressure, water
  2. additionwas added
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with saturated brine
  5. customdried
  6. additionby adding sodium sulfate
  7. customThe solvent was evaporated under reduced pressure, and methanol
  8. additionwas added to the obtained residue
  9. customThe mixture was crystallized

Sources & evidence

ORD record
ord-b66deafdf04e4e3f9a20f2bd8b5dca05
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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