Citric Acid → HCID 22176007, compound

HRID 1797752Notes

Reaction equation

HRID 1797752 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:11]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:12](=[O:30])[C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][C:16]([CH2:26][C:27]([OH:29])=O)=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].O[N:37]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[N:11]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:12](=[O:30])[C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][C:16]([CH2:26][C:27]([NH2:37])=[O:29])=[CH:15][CH:14]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 22175333HCID 22175333, compound

Product 1

HCID 22176007HCID 22176007, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl)acetic acid (0.15 g, 0.32 mmol), 1-hydroxybenzotriazole ammonium salt (0.074 g, 0.48 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.093 g, 0.48 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 17 h. The reaction mixture was poured into 0.1N aqueous citric acid solution (50 mL) and extracted with ethyl acetate (25 mL×2). The organic layers were combined, washed with 0.1N aqueous citric acid solution (50 mL), saturated aqueous sodium hydrogencarbonate (50 mL), and brine (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give tert-butyl[6-(2-amino-2-oxoethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.12 g, 81%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate (25 mL×2)
  2. washwashed with 0.1N aqueous citric acid solution (50 mL), saturated aqueous sodium hydrogencarbonate (50 mL), and brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4d3c470460b141ae8b52d32b930c2ea8
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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