Carbon Dioxide → HCID 59712425, compound

HRID 2222457Notes

Reaction equation

HRID 2222457 reaction equation
[Cl-].[NH3+:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][C:8]1([C:13]([O:15]C)=[O:14])[CH2:12][CH2:11][CH2:10][O:9]1.[C:20](=[O:23])([O-])[O-:21].[Cs+].[Cs+].C(=O)=O.[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>[F:29][C:30]([F:39])([F:40])[C:31]1[CH:38]=[CH:37][C:34]([CH2:35][O:21][C:20]([NH:2][CH2:3][C:4]2[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=2)[CH2:7][C:8]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10][O:9]2)=[O:23])=[CH:33][CH:32]=1

Participants

9

Reactant 4

HCID 280Carbon Dioxide2×HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 86596096HCID 86596096, compound

Product 1

HCID 59712425HCID 59712425, compound

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.020 g of methyl 2-[3-(ammoniomethyl)benzyl]tetrahydro-2-furancarboxylate chloride in 0.5 ml of N,N-dimethylformamide were added 0.064 g of cesium carbonate and 0.046 g of tetrabutylammonium iodide, and dry ice was added thereto little by little over 30 minutes with stirring. 30 μl of 4-trifluoromethylbenzyl bromide was added, and the mixture was stirred for a further 4 hours while adding dry ice. 2 ml of ethyl acetate and 2 ml of water were added, and the organic layer was concentrated. The residue was dissolved in 0.5 ml of ethanol, 0.1 ml of a 5N solution of sodium hydroxide was added, and the mixture was stirred for 14 hours. The reaction mixture was concentrated, and 1 ml of ethyl acetate, 1 ml of water and 0.2 ml of 5N hydrochloric acid were added. The organic layer was concentrated, and the residue was purified by HPLC, to give 0.003 g of the title compound as a white solid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for a further 4 hours
  3. concentrationthe organic layer was concentrated
  4. dissolutionThe residue was dissolved in 0.5 ml of ethanol
  5. addition0.1 ml of a 5N solution of sodium hydroxide was added
  6. stirringthe mixture was stirred for 14 hours
  7. concentrationThe reaction mixture was concentrated
  8. addition1 ml of ethyl acetate, 1 ml of water and 0.2 ml of 5N hydrochloric acid were added
  9. concentrationThe organic layer was concentrated
  10. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-c2ce342062424de28968c59650536c8c
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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