Hydrochloric Acid → HCID 54725316, compound

HRID 1797569Notes

Reaction equation

HRID 1797569 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.C(O)C.[O-]CC.[Na+].Cl.[CH2:28]([NH:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:29]([CH3:31])[CH3:30].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[O-]CC.[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([C:13]([OH:15])=[C:33]([C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[N:32]([CH2:28][CH:29]([CH3:31])[CH3:30])[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

10

Reactant 7

HCID 313Hydrochloric Acid2×HCID 757711-HydroxybenzotriazoleHCID 2723922Sodium ethoxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11030552HCID 11030552, compoundHCID 16097937HCID 16097937, compoundHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 54725316HCID 54725316, compoundYield 9.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 4-benzyloxyphthalic anhydride (2.54 g, 10 mmol) in ethanol (30 mL) was added 20% sodium ethoxide ethanol solution (3.74 g, 11 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 tert-butyl 2-(isobutylamino)acetate (2.25 g, 12 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g, 12 mmol) and 1-hydroxybenzotriazole (1.84 g, 12 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 ethanol (30 mL) and a solution (6.80 g, 20 mmol) of 20% sodium ethoxide in ethanol was added thereto. The mixture was stirred at room temperature for 1 h. The reaction mixture was poured into 1N hydrochloric acid (20 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 tert-butyl 7-benzyloxy-4-hydroxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (0.40 g, 9.5%) 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 ethanol (30 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-ba8f86bce23d44da9f4ee72d42cd7879
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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