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

HRID 1816553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816553
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 10906522Ethyl 2-ethoxy-3-(4-methoxy-3-(([4-(trifluoromethyl)benzyl)amino)carbonyl)phenyl)propanoateAusbeute 72,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2d67b5a765234ea198b006bb6cf5a79e
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884821B1

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