Oxalyl chloride → HCID 22261895, 화합물

HRID 1610202

반응식

HRID 1610202 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([OH:15])=O)=[CH:8][CH:7]=[CH:6]2.C(Cl)(=O)C(Cl)=O.Cl.[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([OH:44])[CH:31]([NH2:43])[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C.O.CN(C)C=O>[F:23][C:24]1[CH:25]=[CH:26][C:27]([CH:30]([OH:44])[CH:31]([NH:43][C:13]([C:9]2[C:10]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=3)[CH:6]=[CH:7][CH:8]=2)=[O:15])[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[CH:28][CH:29]=1

참가 물질

9

반응물 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 44137086-Methoxy-1-naphthoic acidHCID 22261728HCID 22261728, 화합물

생성물 1

HCID 22261895HCID 22261895, 화합물수율 69.2%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-methoxy-1-naphthalenecarboxylic acid (129 mg, 0.64 mmol) in tetrahydrofuran (5 ml) were added oxalyl chloride (0.11 ml, 1.28 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 (150 mg, 0.43 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=2:1) and recrystallized from ethyl acetate-hexane to give the title compound (148 mg, 69%).

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=2:1)
  8. customrecrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-acad8b1652d548f1a3499623cdaec0d0
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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