Water → HCID 68819021, compound

HRID 1785350Notes

Reaction equation

HRID 1785350 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:5])[CH3:2].C(=O)([O-])[O-:26].[K+].[K+].[CH3:31][N:32]([CH3:36])[C:33](Cl)=[O:34].O>CN(C)C=O>[CH3:31][N:32]([CH3:36])[C:33]([O:17][C:13]1([OH:26])[CH:14]=[CH:15][C:16]2[CH:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:8]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:9][CH2:10][C:11]=2[CH2:12]1)=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 17861970HCID 17861970, compound

Product 1

HCID 68819021HCID 68819021, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of t-butyl 1-ethoxycarbonylmethyl-6-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylate (1.70 g, 5.07 mmol) synthesized in step (d) of Example 187 in dimethylformamide (5 ml) were added potassium carbonate (1.03 g, 7.50 mmol) and N,N-dimethylcarbamoyl chloride (0.69 ml, 7.5 mmol), and the resulting mixture was stirred for 2.5 hours at room temperature under a nitrogen atmosphere. After stirring, water (20 ml) was added, and the resulting mixture was extracted with ethyl acetate (20 ml×2). The organic layer was washed with saturated aqueous sodium chloride solution (30 ml×1), dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (2:1-1:1) as the eluent to afford the title compound (1.97 g, yield: 95%) as a colorless oil.

Workup

  1. stirringAfter stirring
  2. extractionthe resulting mixture was extracted with ethyl acetate (20 ml×2)
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution (30 ml×1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford the crude product
  8. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-5eb99a98074542cdac0a1b8b4ef922f8
Source dataset
uspto-grants-2009_03
Patent number
US07504437B2

Reaction notes

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