Potassium Carbonate → HCID 57558093, compound

HRID 1162927Notes

Reaction equation

HRID 1162927 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13]([C@H:15]3[C@@H:19]([CH2:20]Br)[O:18][C:17]([CH3:23])([CH3:22])[O:16]3)=[O:14])[CH:10]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[NH:3]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:22][C:17]1([CH3:23])[O:18][C@@H:19]2[CH2:20][N:12]([C:9]3[CH:10]=[C:11]4[C:6]([CH:5]=[C:4]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[C:30]([F:33])([F:32])[F:31])[NH:3][C:2]4=[O:1])=[CH:7][CH:8]=3)[C:13](=[O:14])[C@@H:15]2[O:16]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57557953HCID 57557953, compound

Product 1

HCID 57558093HCID 57558093, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The (4R,5S)-5-bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-carboxylic acid [1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]amide (3.0 g, 5.71 mmol) obtained in step B was dissolved in anhydrous DMF (50 ml), and potassium carbonate (3.95 g, 28.6 mmol) was then added thereto. The obtained mixture was stirred at a room temperature for 2 hours. Thereafter, the solvent was distilled away. Water and ethyl acetate were added to the obtained residue. An organic layer was separated, and a water layer was extracted with ethyl acetate. The organic layer was mixed with the extract. The obtained mixture was washed with water and a saturated saline solution, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=70:1 to 20:1), so as to obtain 640 mg of 7-((3aR,6aR)-2,2-dimethyl-4-oxotetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (25%).

Workup

  1. distillationThereafter, the solvent was distilled away
  2. additionWater and ethyl acetate were added to the obtained residue
  3. customAn organic layer was separated
  4. extractiona water layer was extracted with ethyl acetate
  5. additionThe organic layer was mixed with the extract
  6. washThe obtained mixture was washed with water
  7. dry with materiala saturated saline solution, and was then dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled away under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=70:1 to 20:1)

Sources & evidence

ORD record
ord-46f5cefaa15c475b80042449cfaa0466
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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