Tetrahydrofuran → HCID 66906070, Verbindung

HRID 1691759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691759
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[CH2:14][N:15]([C@@H:23]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:24])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].[F:35][C:36]1[CH:37]=[C:38]([CH:43]=[C:44]([F:47])[C:45]=1F)[C:39]([O:41][CH3:42])=[O:40].C(=O)([O-])[O-].[K+].[K+].C1COCC1>O.CS(C)=O>[C:18]([O:17][C:16]([N:15]([CH2:14][C@@H:9]1[C@@H:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:13][CH2:12][N:11]([C:45]2[C:44]([F:47])=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][C:36]=2[F:35])[CH2:10]1)[C@@H:23]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:24])=[O:22])([CH3:19])([CH3:21])[CH3:20]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 2783211Methyl 3,4,5-trifluorobenzoateHCID 59178528HCID 59178528, Verbindung

Produkt 1

HCID 66906070HCID 66906070, VerbindungAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 191 mg of tert-butyl {[4-(2-fluorophenyl)piperidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate, 118 mg of methyl 3,4,5-trifluorobenzoate, 114 mg of potassium carbonate, and 2.0 mL of THF-2.0 mL of DMSO was stirred at 100° C. overnight. After cooling, to the reaction mixture was added water, followed by extraction with ethyl acetate, and then drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 147 mg of methyl 4-[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-(2-fluorophenyl)piperidin-1-yl]-3,5-difluorobenzoate as a colorless amorphous substance.

Aufarbeitung

  1. temperatureAfter cooling, to the reaction mixture
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c0b7a3222eb7452289e147680bc383d1
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153658B2

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