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Water → Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({4'-[(methoxycarbonyl)methyl]-2'-nitro-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

HRID 2076705
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HRID 2076705 반응식
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=2[N+:25]([O-:27])=[O:26])=[CH:10][CH:9]=1.Br[CH2:29][C:30]1[C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[C:34]([O:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:33]([C:51]([F:54])([F:53])[F:52])=[CH:32][CH:31]=1.O>CC(C)=O>[C:47]([O:46][C:44]([O:43][C:34]1[C:33]([C:51]([F:52])([F:53])[F:54])=[CH:32][CH:31]=[C:30]([CH2:29][O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=3[N+:25]([O-:27])=[O:26])=[CH:10][CH:9]=2)[C:35]=1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:45])([CH3:48])([CH3:49])[CH3:50]
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoateHCID 86088130Methyl (4'-hydroxy-2-nitro-1,1'-biphenyl-4-yl)acetate

생성물 1

HCID 67119306Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({4'-[(methoxycarbonyl)methyl]-2'-nitro-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

시약·촉매·용매 1

HCID 180Acetone용매

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온도
70 °C

실험 절차

Potassium carbonate (147 mg, 1.06 mmol) was added to a solution of methyl (4′-hydroxy-2-nitro-1,1′-biphenyl-4-yl)acetate (203 mg, 0.71 mmol) obtained in Example (37-1) and tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (330 mg, 0.781 mmol) obtained in Example (28-5) in acetone (15 ml), and the mixture was stirred at 70° C. for 8 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was subjected to silica gel column chromatography (eluting solvent: hexane/ethyl acetate=4/1) to give crude tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({4′-[(methoxycarbonyl)methyl]-2′-nitro-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent under reduced pressure
  6. washwas subjected to silica gel column chromatography (eluting solvent: hexane/ethyl acetate=4/1)

출처 및 근거

ORD 기록
ord-712de128d4994735aad882b5fa2d1d43
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07923573B2

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