Dichloromethane → Tert-butyl 2-[(diphenylmethylene)amino]-3-[4-(trifluoromethoxy)phenyl]propanoate

HRID 1799293Notes

Reaction equation

HRID 1799293 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.C(Cl)Cl.[C:17]1([C:23](=[N:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:17]1([C:23](=[N:30][CH:31]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=2)[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 688171N-(Diphenylmethylene)glycine tert-butyl ester

Product 1

HCID 86636533Tert-butyl 2-[(diphenylmethylene)amino]-3-[4-(trifluoromethoxy)phenyl]propanoateYield 78%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

1-(Bromomethyl)-4-(trifluoromethoxy)benzene (1.23 mL, 7.7 mmol) and tetrabutylammonium hydrogen sulfate (2.85 g, 8.4 mmol) were added to a methylene chloride (50 mL) solution of tert-butyl [(diphenylmethylene)amino]acetate (compound described in J. Org. Chem., (1982), 47, 2663-2666, 2.07 g, 7.0 mmol) at room temperature according to the method described in the document (J. Org. Chem., (1995), 60, 601-607), and subsequently a 10% sodium hydroxide aqueous solution (21 mL) was added thereto. The mixture was vigorously stirred for 1.5 hours, and then to the reaction solution was added water. The resulting mixture was extracted with methylene chloride. The organic layer was collected, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (n-hexane to n-hexane:ethyl acetate, 19:1 and 9:1, V/V) twice to give 2.55 g of the title compound (white powder, yield: 78%).

Workup

  1. extractionThe resulting mixture was extracted with methylene chloride
  2. customThe organic layer was collected
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by silica gel column chromatography (n-hexane to n-hexane:ethyl acetate, 19:1 and 9:1, V/V) twice

Sources & evidence

ORD record
ord-239dc31af3204489b7f4abdcc31b01f4
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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