Potassium Carbonate → HCID 86610930, compound

HRID 2219213Notes

Reaction equation

HRID 2219213 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[NH:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CN(C=O)C>[CH3:33][O:32][C:30](=[O:31])[CH2:29][N:21]([C:15]1[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=1[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:22](=[O:27])[C:23]([F:26])([F:24])[F:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 86610929HCID 86610929, compound

Product 1

HCID 86610930HCID 86610930, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Powdered potassium carbonate (1.10 g, 7.97 mmol) is added to a stirred solution of N-(2-benzyl-4-chloro-phenyl)-2,2,2-trifluoro-acetamide (1.25 g, 3.98 mmol) and methyl bromoacetate (1.34 g, 8.76 mmol) in anhydrous DMF (5 mL). The resultant mixture is stirred at ambient temperature under nitrogen for 2 hours. After dilution with EtOAc (60 mL), the mixture is washed with water (25 mL×3), dried over MgSO4, filtered, concentrated and chromatographed on-silica (gradient 0-15% EtOAc in hexane) to give 1.37 g (3.55 mmol, 89% yield) of the title compound as oil. ESIMS: m/z 386 [(M+H)+, 35Cl], 388 [(M+H)+, 37Cl].

Workup

  1. washAfter dilution with EtOAc (60 mL), the mixture is washed with water (25 mL×3)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on-silica (gradient 0-15% EtOAc in hexane)

Sources & evidence

ORD record
ord-492d96a7f00f443cac822a1c857e63e5
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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