Hydrochloric Acid → HCID 10271081, compound

HRID 1797577Notes

Reaction equation

HRID 1797577 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[N:10]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:11](=[O:30])[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]([O:25][CH2:26][C:27]([NH2:29])=[O:28])=[CH:14][CH:13]=2)(C)(C)C.Cl>C(OCC)(=O)C>[NH2:7][CH2:8][C:9]1[N:10]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:11](=[O:30])[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]([O:25][CH2:26][C:27]([NH2:29])=[O:28])=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22175855HCID 22175855, compound

Product 1

HCID 10271081HCID 10271081, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl[6-(2-amino-2-oxoethoxy)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.38 g, 0.8 mmol) in ethyl acetate (5 mL) was added a solution of 4N hydrogen chloride in ethyl acetate (5 mL) and the obtained solution was stirred at room temperature for 2 h. The reaction, mixture was concentrated under reduced pressure, and the residue was suspended in 1N aqueous sodium hydroxide solution. The suspension was stirred at room temperature for 10 min, and 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 precipitated crystals were recrystallized from ethyl acetate-diisopropyl ether to give 2-[[3-(aminomethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl]oxy]acetamide (0.19 g, 63.3%) as crystals.

Workup

  1. customThe reaction, mixture
  2. concentrationwas concentrated under reduced pressure
  3. stirringThe suspension was stirred at room temperature for 10 min
  4. additionthe reaction mixture was poured into water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe precipitated crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-a0385696b1bf45ff8b8cb949d329196c
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…