Hydrochloric Acid → HCID 54725309, compound

HRID 1797540Notes

Reaction equation

HRID 1797540 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[O:17])[O:15][C:13](=O)[C:12]2=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C[O-].[Na+].Cl.[CH2:26]([NH:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:27]([CH3:29])[CH3:28].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CO.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([C:13]([OH:15])=[C:31]([C:32]([O:34][CH3:35])=[O:33])[N:30]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:16]2=[O:17])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 313Hydrochloric Acid2×HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16097937HCID 16097937, compoundHCID 22175789HCID 22175789, compoundHCID 23694274Sodium methanolate methanol2×

Product 1

HCID 54725309HCID 54725309, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4-benzyloxyphthalic anhydride (25.42 g, 100 mmol) in methanol (200 mL) was added 28% sodium methoxide methanol solution (21.22 g, 110 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into 1N hydrochloric acid (150 mL) 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 N,N-dimethylformamide (200 mL) and methyl 2-(isobutylamino)acetate (17.42 g, 120 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (23.00 g, 120 mmol) and 1-hydroxybenzotriazole (18.34 g, 120 mmol) were added, and the mixture was stirred at room temperature for 3 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 dissolved in methanol (50 mL) and a solution of 28% sodium methoxide methanol solution (38.59 g, 200 mmol) was added thereto. The mixture was stirred at room temperature for 1 h. The reaction mixture was poured into 1N hydrochloric acid (200 mL) 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 and the component eluted earlier was concentrated to give methyl 7-benzyloxy-4-hydroxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (4.76 g, 12.1%) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in N,N-dimethylformamide (200 mL)
  6. stirringthe mixture was stirred at room temperature for 3 h
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. dissolutionThe residue was dissolved in methanol (50 mL)
  12. stirringThe mixture was stirred at room temperature for 1 h
  13. extractionextracted with ethyl acetate
  14. washThe extract was washed with brine
  15. dry with materialdried over anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by silica gel column chromatography
  18. washthe component eluted earlier
  19. concentrationwas concentrated

Sources & evidence

ORD record
ord-88cac3852fc04b898fefe6167d83f3af
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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