Dimethylformamide → HCID 59715645, compound

HRID 2078005Notes

Reaction equation

HRID 2078005 reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].[C:8]12([CH2:18]S(O)(=O)=O)[C:15]([CH3:17])(C)[CH:12]([CH2:13][CH2:14]1)[CH2:11][C:9]2=O.C(=O)([O-])[O-].[Na+].[Na+].[CH3:29][N:30]([CH3:33])C=O>>[CH3:4][C:3]1([CH3:5])[O:6][CH:7]([C:17]#[C:15][C:12]2[CH:11]=[CH:9][C:8]([CH2:18][C:29]3[C:14]4[C:8](=[CH:9][CH:11]=[CH:12][CH:13]=4)[CH:15]=[CH:33][N:30]=3)=[CH:14][CH:13]=2)[CH2:1][O:2]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 64952,2-DimethoxypropaneHCID 10340Sodium CarbonateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

Product 1

HCID 59715645HCID 59715645, compound

Conditions

Temperature
75 °C

Procedure

2,2-Dimethoxypropane (0.36 ml), 10-camphorsulfonic acid (43 mg), and molecular sieves (4 Å) were added to a solution of the compound of Example B109 (34 mg) in dimethylformamide (2 ml), and this reaction mixture was stirred at 75° C. for 9 hours. After an saturated aqueous sodium carbonate solution was added, the reaction mixture was extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (14 mg).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2aff0b9346a943299421f578e2e52beb
Source dataset
uspto-grants-2011_04
Patent number
US07928209B2

Reaction notes

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