Ammonium Chloride → (-)-2-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxamide

HRID 1799019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799019
C(N1[CH:7]=[C:6]([C:8]2[CH:20]=[C:19]([C:21](O)=O)[C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]([OH:28])([C:24]([F:27])([F:26])[F:25])[C:10]=3[CH:9]=2)[CH:5]=[N:4]1)C.Cl.CN(C)[CH2:32][CH2:33]CN=C=NCC.[OH2:41].O[N:43]1C2C=CC=CC=2N=N1.[Cl-].[NH4+:53]>C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[CH2:32]([N:53]1[CH:7]=[C:6]([C:8]2[CH:20]=[C:19]([C:21]([NH2:43])=[O:41])[C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]([OH:28])([C:24]([F:25])([F:27])[F:26])[C:10]=3[CH:9]=2)[CH:5]=[N:4]1)[CH3:33]

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 594931002-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxylic acid

Produkt 1

HCID 46191680(-)-2-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of an optically active form (0.051 g) of 2-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxylic acid, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.038 g), 1-hydroxybenzotriazole hydrate (0.030 g), ammonium chloride (0.022 g) and dimethylformamide (1 ml) was added triethylamine (0.055 ml), and the mixture was stirred at room temperature overnight. To the reaction mixture was added ethyl acetate (10 ml), and the organic layer was successively washed once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate, 3 times with water and once with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound (0.043 g, 85%).

Aufarbeitung

  1. washthe organic layer was successively washed once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate, 3 times with water and once with saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d40adeba5ec84be1a01acbbb6d994a33
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343994B2

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