Hydrochloric Acid → HCID 54725281, compound

HRID 1797584Notes

Reaction equation

HRID 1797584 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.[CH2:20]([NH:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:21]([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].C(I)C.[O-]CC.[Na+].Cl>O1CCCC1.C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([C:13]([OH:15])=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:24]([CH2:20][CH:21]([CH3:22])[CH3:23])[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 6

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2723922Sodium ethoxideHCID 10877410N-(2-Methylpropyl)glycine ethyl esterHCID 16097937HCID 16097937, compound

Product 1

HCID 54725281HCID 54725281, compoundYield 66.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-benzyloxyphthalic anhydride (4.07 g, 16 mmol) and ethyl 2-(isobutylamino)acetate (2.86 g, 18 mmol) in tetrahydrofuran (30 mL) 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 dissolved in N,N-dimethylformamide (30 mL), and potassium carbonate (2.21 g, 16 mmol) and ethyl iodide (1.5 mL, 19.2 mmol) were added thereto. 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 (50 mL), and a solution (10.9 g, 32 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 (70 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 ethyl 7-benzyloxy-4-hydroxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (4.21 g, 66.6%) 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 (30 mL)
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe residue was dissolved in ethanol (50 mL)
  11. stirringThe mixture was stirred at room temperature for 1 h
  12. extractionextracted with ethyl acetate
  13. washThe extract was washed with brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe residue was purified by silica gel column chromatography
  17. washthe component eluted earlier
  18. concentrationwas concentrated

Sources & evidence

ORD record
ord-c85a041ff31443c4840afe7b033f44ab
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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