Water → HCID 22176142, compound

HRID 1797753Notes

Reaction equation

HRID 1797753 reaction equation
CS(O[CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][C:19]([CH3:22])(C)[CH3:20])[C:11]([CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:10]2OCCCC)(=O)=O.[C:37]1(=[O:47])[NH:41][C:40](=[O:42])[C:39]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]12.[K].O>CN(C)C=O>[C:28]([O:27][C:25](=[O:26])[NH:24][CH2:23][C:11]1[N:12]([CH2:18][CH:19]([CH3:20])[CH3:22])[C:13](=[O:17])[C:14]2[C:9]([C:10]=1[C:7]1[CH:8]=[CH:9][CH:14]=[CH:15][CH:16]=1)=[CH:8][C:7]([CH2:6][N:41]1[C:37](=[O:47])[C:38]3[C:39](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:40]1=[O:42])=[CH:16][CH:15]=2)([CH3:29])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 22176289HCID 22176289, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 22176142HCID 22176142, compoundYield 165.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-{[(tert-butoxycarbonyl)amino]methyl}-4-butoxy-2-neopentyl-1-oxo-1,2-dihydro-6-isoquinolinyl)methyl methanesulfonate (1.1 g, 2.11 mmol) in N,N-dimethylformamide (20 mL) was added potassium phthalimide (0.47 g, 2.5 mmol), and the mixture was stirred at room temperature for 17 h. The reaction mixture was poured into water (200 mL) and extracted with ethyl acetate (100 mL×2). The organic layers were combined, washed with 0.2N hydrochloric acid (100 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 (n-hexane:ethyl acetate=5:2 (v/v)) to give tert-butyl{6-[(1,3-dioxo-1,3-dihydro-2H -isoindol-2-yl)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.99 g, 84%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate (100 mL×2)
  2. washwashed with 0.2N hydrochloric acid (100 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 (n-hexane:ethyl acetate=5:2 (v/v))

Sources & evidence

ORD record
ord-a2d08c38c8694b10aaf0a3bbeb2591f7
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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