Benzenepropanoyl chloride → N-((1RS,2SR)-2-hydroxy-2-(3-phenoxyphenyl)-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-3-phenylpropanamide

HRID 1610461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610461
[NH2:1][CH:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)[CH:3]([C:5]1[CH:10]=[CH:9][C:8](OC2C=CC=CC=2)=[CH:7][CH:6]=1)[OH:4].[C:29]1([CH2:35][CH2:36][C:37](Cl)=[O:38])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:40](=[O:43])([O-])O.[Na+]>C(OCC)(=O)C.O>[OH:4][CH:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([O:43][C:40]2[CH:19]=[CH:18][CH:2]=[CH:3][CH:5]=2)[CH:10]=1)[CH:2]([NH:1][C:37](=[O:38])[CH2:36][CH2:35][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 64801Benzenepropanoyl chlorideHCID 516892Sodium BicarbonateHCID 22261609(1RS,2SR)-2-amino-1-(4-phenoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol

Produkt 1

HCID 22261717N-((1RS,2SR)-2-hydroxy-2-(3-phenoxyphenyl)-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-3-phenylpropanamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (1RS,2SR)-2-amino-1-(4-phenoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol (400 mg, 1.03 mmol) in ethyl acetate (20 ml) were added 3-phenylpropionyl chloride (230 ml, 1.55 mmol) and saturated aqueous sodium hydrogen carbonate (20 ml), and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (100 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (472 mg, 88%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-7bdf5c855bf94a8c829122b486b47c05
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

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