Water → HCID 178498873, compound

HRID 1797759Notes

Reaction equation

HRID 1797759 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][C:9]1[N:10]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:11](=[O:29])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25]([NH2:28])=[N:26]O)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:42][O:43][C:44](=[O:47])[CH2:45][CH3:46].O>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[N:10]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:11](=[O:29])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25]1[NH:28][CH:46]=[C:45]([C:44]([O:43][CH3:42])=[O:47])[N:26]=1)=[CH:14][CH:13]=2)=[O:34])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11124Methyl propionateHCID 86592078HCID 86592078, compound

Product 1

HCID 178498873HCID 178498873, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of tert-butyl{6-[amino(hydroxyimino)-methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.47 g, 1.0 mmol) and triethylamine (0.17 mL, 1.2 mmol) in ethyl acetate (10 mL) was added methylpropionate (0.10 g, 1.2 mmol), and the mixture was stirred at room temperature for 17 h. The reaction mixture was poured into water (5 mL), and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue was added p-xylene (10 mL), the mixture was refluxed for 40 h. The reaction mixture was diluted with ethyl acetate (100 mL), and the solution was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 (v/v)) to give methyl 2-(3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl)-1H-imidazole-4-carboxylate (0.22 g, 42%) as an orange powder.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added p-xylene (10 mL)
  5. temperaturethe mixture was refluxed for 40 h
  6. additionThe reaction mixture was diluted with ethyl acetate (100 mL)
  7. washthe solution was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 (v/v))

Sources & evidence

ORD record
ord-ce93b85fed8d4728887f7853454b2575
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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