Hydrochloric Acid → N-(2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-(2-thienyl)butyramide

HRID 1610169노트

반응식

HRID 1610169 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:32])[CH:9]([NH:21][C:22](=[O:31])[CH2:23][CH2:24][CH2:25][C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO.[Cl-].[Mn+2].[Cl-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:32])[CH:9]([NH:21][C:22](=[O:31])[CH2:23][CH2:24][CH2:25][C:26]2[S:27][CH:28]=[CH:29][CH:30]=2)[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:20])[F:19])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22261648N-(2-(4-fluorophenyl)-2-oxo-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-(2-thienyl)butyramide

생성물 1

HCID 22261950N-(2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-(2-thienyl)butyramide수율 68%

시약·촉매·용매 2

HCID 10313134Manganese(2+) dichloride촉매HCID 887Methanol용매

실험 절차

To a solution of N-(2-(4-fluorophenyl)-2-oxo-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-(2-thienyl)butyramide (300 mg, 0.65 mmol) in methanol (30 ml) was added manganese (II) chloride (163 mg, 1.30 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction solution was added sodium borohydride (49 mg, 1.30 mmol) under ice-cooling, and the mixture was stirred for 1 hr. The reaction solution was poured into 1N hydrochloric acid (30 ml) and extracted with ethyl acetate (50 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), and the obtained crude crystal was washed with a mixed solvent of hexane:ethyl acetate=10:1 to give the title compound ((1RS,2SR) form: (1RS,2RS) form=1:1, 204 mg, 68%).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. washThe extract was washed with water and 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=2:1)
  8. customthe obtained crude crystal
  9. washwas washed with a mixed solvent of hexane

출처 및 근거

ORD 기록
ord-6754a36696594cd0b81f7bbe9fb9fb53
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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