Water → HCID 60206120, compound

HRID 1797564Notes

Reaction equation

HRID 1797564 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH:17]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[N:24]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:23]([CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[C:22]2[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=O.O>CN(C)C=O>[C:38]([O:37][C:36]([NH:35][CH2:34][C:23]1[N:24]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:25](=[O:29])[C:26]2[C:21]([C:22]=1[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[CH:20][C:19](/[CH:17]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:28][CH:27]=2)=[O:42])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 22175466HCID 22175466, compound

Product 1

HCID 60206120HCID 60206120, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl diethylphosphonoacetate (1.0 mL, 5 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (0.20 g, 5 mmol) (60% in oil), and the mixture was stirred at room temperature for 10 min. To the obtained mixture was added a solution of tert-butyl (6-formyl-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (2.17 g, 5 mmol) in N,N-dimethylformamide (20 mL) and the mixture was stirred at room temperature for 1 h. 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 obtained crystals were recrystallized from ethyl acetate-diisopropyl ether to give ethyl (E)-3-[3-[[(tert-butoxycarbonyl)amino]methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinyl]-2-propenate (2.03 g, 71.7%) as an amorphous.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-fb893f8c565b481bbb36fd37c3e94685
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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