Hydrogen Bromide → HCID 22175326, compound

HRID 1797636Notes

Reaction equation

HRID 1797636 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][CH2:8][C:9]1[N:10]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:11](=[O:34])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[CH:16][C:15]([O:26]CC1C=CC=CC=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].Br.[OH-].[Na+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O>[C:1]([O:5][C:6](=[O:39])[NH:7][CH2:8][C:9]1[N:10]([CH2:35][CH:36]([CH3:37])[CH3:38])[C:11](=[O:34])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)=[CH:16][C:15]([OH:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 22176049HCID 22176049, compound

Product 1

HCID 22175326HCID 22175326, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tert-butyl[6-benzyloxy-4-(4-chlorophenyl)-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.54 g, 1 mmol) was suspended in 48% aqueous solution (20 ml) of hydrogen bromide and the obtained mixture was refluxed under heating for 3 h. The reaction mixture was neutralized with 1N sodium hydroxide aqueous solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 ml) and di-t-butyl dicarbonate (0.28 ml, 1 mmol) was added thereto. The obtained mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl[4-(4-chlorophenyl)-6-hydroxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.32 g, 71.1%) as crystals.

Workup

  1. temperaturethe obtained mixture was refluxed
  2. temperatureunder heating for 3 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in tetrahydrofuran (10 ml)
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fd9051bdc81d455eaa8460d52a07c022
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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