Triethylamine → Ethyl 2-ethoxy-3-(4-methoxy-3-(([4-(trifluoromethyl)benzyl)amino)carbonyl)phenyl)propanoate

HRID 1816553Notes

Reaction equation

HRID 1816553 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([O:18][CH2:19][CH3:20])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:16][CH3:17])=[C:11]([CH:15]=1)[C:12]([OH:14])=O)[CH3:2].[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O.O>[CH2:19]([O:18][CH:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:16][CH3:17])=[C:11]([C:12]([NH:29][CH2:28][C:27]2[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:32])[F:33])=[CH:31][CH:30]=2)=[O:14])[CH:15]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 768044-(Trifluoromethyl)benzylamineHCID 109134625-(3-Ethoxy-2-ethoxy-3-oxopropyl)-2-methoxybenzoic acid

Product 1

HCID 10906522Ethyl 2-ethoxy-3-(4-methoxy-3-(([4-(trifluoromethyl)benzyl)amino)carbonyl)phenyl)propanoateYield 72.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.58 g of 5-(3-ethoxy-2-ethoxy-3-oxopropyl)-2-methoxybenzoic acid and 0.34 g of 4-(trifluoromethyl)benzylamine were dissolved in 7 ml N,N-dimethylformamide, and 0.30 ml diethyl cyanophosphonate and 0.27 ml triethylamine were added thereto under ice-cooling. The reaction mixture was stirred at room temperature for 16 hours, then poured into iced water and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and brine in this order, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (3:1), 0.64 g of ethyl 2-ethoxy-3-(4-methoxy-3-(([4-(trifluoromethyl)benzyl)amino)carbonyl)phenyl)propanoate was obtained.

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid and brine in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. washfrom fractions eluted with hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-2d67b5a765234ea198b006bb6cf5a79e
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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