Carbon Dioxide → HCID 57719474, compound

HRID 1985296Notes

Reaction equation

HRID 1985296 reaction equation
[Cl-].[NH3+:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][CH:11]([O:17][CH:18]([CH3:20])[CH3:19])[C:12]([O:14]CC)=[O:13])[CH:7]=[CH:8][CH:9]=1.[C:21](=[O:23])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+].[F:30][C:31]([F:41])([F:40])[C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35]Br>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH:18]([O:17][CH:11]([CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][NH:2][C:21]([O:23][CH2:35][C:34]2[CH:37]=[CH:38][CH:39]=[C:32]([C:31]([F:30])([F:40])[F:41])[CH:33]=2)=[O:22])[CH:5]=1)[C:12]([OH:14])=[O:13])([CH3:19])[CH3:20]

Participants

8

Reactant 4

HCID 280Carbon Dioxide2×HCID 10796Cesium carbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 22926990HCID 22926990, compound

Product 1

HCID 57719474HCID 57719474, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

20 mg of Ethyl 3-[3-(ammoniomethyl)phenyl]-2-isopropoxypropanoate chloride was dissolved in 0.5 ml of N,N-dimethylformamide which was saturated in advance with carbon dioxide by adding dry ice, and 150 mg of cesium carbonate and 200 mg of tetrabutylammonium iodide were added, and the mixture was stirred at room temperature for 30 minutes. 40 mg of 3-trifluoromethylbenzyl bromide was added, and stirring was continued at room temperature for 3 hours. To the reaction mixture was added ethyl acetate, and the mixture was washed with water. The solvent was concentrated, and the residue was treated with 0.4 ml of ethanol and 0.1 ml of 5N-sodium hydroxide, and the mixture was kept still at room temperature for 30 minutes. The solution was neutralized with 1N-hydrochloric acid, and extracted with ethyl acetate. The solvent was distilled off, and the residue was purified by reverse-phase high performance liquid chromatography, to give 1.09 mg of the title compound.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitwas continued at room temperature for 3 hours
  4. washthe mixture was washed with water
  5. concentrationThe solvent was concentrated
  6. additionthe residue was treated with 0.4 ml of ethanol and 0.1 ml of 5N-sodium hydroxide
  7. waitthe mixture was kept still at room temperature for 30 minutes
  8. extractionextracted with ethyl acetate
  9. distillationThe solvent was distilled off
  10. customthe residue was purified by reverse-phase high performance liquid chromatography

Sources & evidence

ORD record
ord-8d67fcadd73a405883481b22d0884012
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

Loading…