Hydrochloric Acid → HCID 22175613, compound

HRID 1797581Notes

Reaction equation

HRID 1797581 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13](/[CH:16]=[CH:17]/[C:18]([O:20]CC)=[O:19])[CH:14]=2)[C:9](=[O:23])[N:8]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:7]=1[CH2:29][NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].O.Cl>O1CCCC1.C(O)C>[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])[CH:14]=2)[C:9](=[O:23])[N:8]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:7]=1[CH2:29][NH:30][C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 60206301HCID 60206301, compound

Product 1

HCID 22175613HCID 22175613, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (E)-3-[4-butoxy-3[[(tert-butoxycarbonyl)amino]methyl]-2-neopentyl-1-oxo-1,2-dihydro-6-isoquinolinyl]-2-propenate (0.67 g, 1.3 mmol) in tetrahydrofuran (5 mL) and ethanol (5 mL) as added 1N sodium hydroxide (3 mL). The obtained mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water, acidified with 1N hydrochloric acid 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-n-hexane to give (E)-3-[4-butoxy-3-[[(tert-butoxycarbonyl)amino]methyl]-2-neopentyl-1-oxo-1,2-dihydro-6-isoquinolinyl]-2-propenic acid (0.53 g, 84.1%) as crystals.

Workup

  1. extractionextracted with ethyl-acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained crystals were recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-0cdc0269907048a8b0c0dcbd6b66258e
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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