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

HRID 1610224

반응식

HRID 1610224 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a18e2610cd2743af800b1984b2fdd2be
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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