Potassium Carbonate → HCID 67455949, compound

HRID 469711Notes

Reaction equation

HRID 469711 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[Br-].[F:10][C:11]([F:19])([F:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I>[F:10][C:11]([F:19])([F:18])[C:12]1[CH:17]=[CH:16][C:15]([N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 86666034HCID 86666034, compound

Product 1

HCID 67455949HCID 67455949, compound

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Conditions

Temperature
90 °C

Procedure

A reaction vessel containing L-proline, 4-trifluoromethylbenzenebromide, potassium carbonate and copper iodide is evacuated and purged with argon several times. Dimethylformamide is added and the solution is heated at 90° C. for 4 days in a sealed vessel. After this time, the mixture is cooled to room temperature and diluted with ethyl acetate and water. The two layers are separated and the aqueous is acidified to pH3 using concentrated hydrochloric acid and extracted with ethyl acetate. The combined organics are washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford title compound as intermediate which is used crude in subsequent reactions. ESI m/z 260 [M+H]+

Workup

  1. customis evacuated
  2. custompurged with argon several times
  3. additionDimethylformamide is added
  4. temperatureAfter this time, the mixture is cooled to room temperature
  5. additiondiluted with ethyl acetate and water
  6. customThe two layers are separated
  7. extractionextracted with ethyl acetate
  8. washThe combined organics are washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e366853c4c084858b8ec1dd80574ea73
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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