Water → HCID 21994140, compound

HRID 1978346Notes

Reaction equation

HRID 1978346 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:19]S(OC)(=O)=O.O>CN(C)C=O>[CH3:19][N:12]([CH2:11][CH2:10][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:13](=[O:18])[C:14]([F:16])([F:17])[F:15]

Participants

6

Reactant 4

HCID 962WaterHCID 4156Methyl MethanesulfonateHCID 24758Sodium hydrideHCID 576337HCID 576337, compound

Product 1

HCID 21994140HCID 21994140, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen, 1.5 g (37.5 mM) of a 60% suspension of sodium hydride in liquid paraffin was added to a solution of 8.0 g (34.6 mM) of N-(3-phenylpropan-1-yl)trifluoroacetamide in N,N-dimethylformamide (70 ml) at 0° C. and the mixture was stirred at the prevailing temperature for 40 minutes. To this reaction mixture was added 3.5 ml (41.3 mM) of methyl methanesulfonate and the mixture was stirred at room temperature for 1.5 hours. Then, water was added to the reaction system to stop the reaction and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over MgSO4, and purified by column chromatography (ethyl acetate-hexane 15%) to provide the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over MgSO4
  6. custompurified by column chromatography (ethyl acetate-hexane 15%)

Sources & evidence

ORD record
ord-a84e7b74a59a4c8bad6227b4e3f67fd7
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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