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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2076705
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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-712de128d4994735aad882b5fa2d1d43
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07923573B2

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