Oxalyl chloride → 4-butyl-N-((1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)benzamide

HRID 1610224

Reaktionsgleichung

Reaktionsgleichung von HRID 1610224
[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C(Cl)(=O)C(Cl)=O.Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([OH:42])[CH:29]([NH2:41])[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C.O.CN(C)C=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:41][CH:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:38])[F:39])=[CH:33][CH:32]=2)[CH:28]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)[OH:42])=[O:11])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

9

Edukt 4

HCID 65578Oxalyl chlorideHCID 886314-Butylbenzoic acidHCID 516892Sodium BicarbonateHCID 22261728(1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride

Produkt 1

HCID 222617454-butyl-N-((1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)benzamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-n-butylbenzoic acid (153 mg, 0.86 mmol) in tetrahydrofuran (5 ml) were added oxalyl chloride (0.15 ml, 1.72 mmol) and N,N-dimethylformamide (0.01 ml), and the mixture was stirred at room temperature for 30 min. The reaction solution was evaporated under reduced pressure. To a solution of the residue in ethyl acetate (5 ml) were added (1RS,2SR)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride (200 mg, 0.57 mmol) and saturated aqueous sodium hydrogen carbonate (5 ml) and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (50 ml), and extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1). Recrystallization from ethyl acetate-hexane gave the title compound (172 mg, 64%).

Aufarbeitung

  1. customThe reaction solution was evaporated under reduced pressure
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1)
  8. customRecrystallization from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-a18e2610cd2743af800b1984b2fdd2be
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

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