Citric Acid → HCID 136376437, compound

HRID 1797675Notes

Reaction equation

HRID 1797675 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][OH:27])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C[C:37](CC(O)=O)(C(O)=O)[OH:38]>C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][C:9]1[N:10]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:11](=[O:29])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][C:15]([C:25]1[NH:28][C:37](=[O:38])[O:27][N:26]=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 86592078HCID 86592078, compound

Product 1

HCID 136376437HCID 136376437, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Tert-butyl{6-[amino(hydroxyimino)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl}methylcarbamate (0.25 g, 0.54 mmol) was dissolved in ethyl acetate (10 ml) and N,N′-carbonyldiimidazole (0.26 g, 1.6 mmol) was added. The mixture was refluxed under heating for 3 h. To the reaction mixture were added 0.1 M aqueous citric acid solution (25 ml) and ethyl acetate (50 ml). The organic layer was washed with 0.1 M aqueous citric acid solution (25 ml), and then saturated brine (25 ml), dried over anhydrous magnesium sulfate (12 g) and concentrated under reduced pressure. The residue was recrystallized from diisopropyl ether-ethyl acetate=2:1 (v/v) to give tert-butyl[2-isobutyl-1-oxo-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.24 g, 93%) as a colorless powder.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 3 h
  3. washThe organic layer was washed with 0.1 M aqueous citric acid solution (25 ml)
  4. dry with materialsaturated brine (25 ml), dried over anhydrous magnesium sulfate (12 g)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from diisopropyl ether-ethyl acetate=2:1 (v/v)

Sources & evidence

ORD record
ord-67948200ec974800b6017cfbd7e5fd19
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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