Dimethylformamide → HCID 59715645, compound

HRID 597776Notes

Reaction equation

HRID 597776 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-b9add24f19a340a0a032660f8b46dec8
Source dataset
uspto-grants-2011_03
Patent number
US07897387B2

Reaction notes

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