Hydrochloric Acid → HCID 22175540, compound

HRID 1797600Notes

Reaction equation

HRID 1797600 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[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]([N:25]1[N:29]=[C:28]([CH3:30])[O:27][CH2:26]1)=[CH:14][CH:13]=2)(C)(C)C.Cl>C(OCC)(=O)C>[NH2:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[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]([N:25]1[N:29]=[C:28]([CH3:30])[O:27][CH2:26]1)=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22176365HCID 22176365, compound

Product 1

HCID 22175540HCID 22175540, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To tert-butyl[2-isobutyl-6-(5-methyl-1,3,4-oxadiazol-3-yl)-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.20 g, 0.41 mmol) was added a solution (4 mL) of 4N hydrogen chloride in ethyl acetate and the mixture was stirred at room temperature for 17 h. The reaction mixture was concentrated under reduced pressure and to the residue was added diisopropyl ether (5 mL). The precipitated powder was collected by filtration. To this powder was added saturated aqueous sodium hydrogencarbonate (30 mL) and the mixture was extracted twice with a solution (25 mL) of ethyl acetate-tetrahydrofuran (1:1). The organic layers were combined and the mixture was washed with saturated brine (25 mL), dried over anhydrous magnesium sulfate (15 g) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1, (v/v)) and recrystallized from n-hexane-ethyl acetate (5:1) to give the title compound (0.11 g, 72%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and to the residue
  2. additionwas added diisopropyl ether (5 mL)
  3. filtrationThe precipitated powder was collected by filtration
  4. additionTo this powder was added saturated aqueous sodium hydrogencarbonate (30 mL)
  5. extractionthe mixture was extracted twice with a solution (25 mL) of ethyl acetate-tetrahydrofuran (1:1)
  6. washthe mixture was washed with saturated brine (25 mL)
  7. dry with materialdried over anhydrous magnesium sulfate (15 g)
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1, (v/v))
  10. customrecrystallized from n-hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-27763d2f5ee44c878df172838be20703
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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