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Water → HCID 67119111, Verbindung

HRID 2076695
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2076695
N1CCOCC1.C([O:10][C:11]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[C:20]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([C:47]([O:49][CH2:50][CH:51]=[CH2:52])=[O:48])=[CH:43][N:44]([CH3:46])[CH3:45])=[C:38]([F:53])[CH:37]=3)=[CH:32][CH:31]=2)[C:12]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])C=C.O>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:10][C:11]1[C:23]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:21]=[C:20]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([C:47]([O:49][CH2:50][CH:51]=[CH2:52])=[O:48])=[CH:43][N:44]([CH3:45])[CH3:46])=[C:38]([F:53])[CH:37]=3)=[CH:32][CH:31]=2)[C:12]=1[C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 8083MorpholineHCID 67119321HCID 67119321, Verbindung

Produkt 1

HCID 67119111HCID 67119111, VerbindungAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Morpholine (0.02 ml, 0.23 mmol) and tetrakis(triphenylphosphine)palladium (0) (6 mg, 0.005 mmol) were successively added to a solution of tert-butyl 2-(allyloxy)-6-{[(4′-{1-[(allyloxy)carbonyl]-2-(dimethylamino)vinyl}-3′-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (67 mg, 0.10 mmol) obtained in Example (93-1) in tetrahydrofuran (1 ml), and the mixture was stirred at room temperature for 1 hour. After the reaction mixture was poured into water and the mixture was 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: n-hexane/ethyl acetate=10/1-1/>99) to give crude tert-butyl 2-hydroxy-6-{[(4′-{1-[(allyloxy)carbonyl]-2-(dimethylamino)vinyl}-3′-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (42 mg).

Aufarbeitung

  1. extractionthe mixture was extracted 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: n-hexane/ethyl acetate=10/1-1/>99)

Quellen und Nachweise

ORD-Eintrag
ord-3e8bdbf2bfb04999b2f812eb2095e7e5
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07923573B2

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