Water → HCID 22175224, compound

HRID 1797637Notes

Reaction equation

HRID 1797637 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[CH:16][C:15]([OH:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:36][C:37]([NH2:39])=[O:38].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)=[CH:16][C:15]([O:26][CH2:36][C:37]([NH2:39])=[O:38])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3727IodoacetamideHCID 24758Sodium hydrideHCID 22175326HCID 22175326, compound

Product 1

HCID 22175224HCID 22175224, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl[4-(4-chlorophenyl)-6-hydroxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.45 g, 1 mmol) in N,N-dimethylformamide (10 ml) was added sodium hydride (48 mg, 1.2 mmol) (60% in oil) at 0° C., and the mixture was stirred at 0° C. for 10 min. To the obtained mixture was added 2-iodoacetamide (0.22 g, 1.2 mmol) and the mixture was stirred at 0° C. for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. After washing the extract with water, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl[6-(2-amino-2-oxoethoxy)-4-(4-chlorophenyl)-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.27 g, 52.9%) as crystals.

Workup

  1. stirringthe mixture was stirred at 0° C. for 2 h
  2. extractionextracted with ethyl acetate
  3. washAfter washing the
  4. extractionextract with water
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a7a0c86551234f938d82e735d43d4d9a
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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