Ethyl Acetate → HCID 89816262, Verbindung

HRID 1500189

Reaktionsgleichung

Reaktionsgleichung von HRID 1500189
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]2([C:32]([F:35])([F:34])[F:33])[CH2:17][CH2:16][N:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[CH:23]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])[CH2:22][CH2:21]4)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C([O:40]C(=O)C)C.C(=O)([O-])O.[Na+]>O.C(#N)C.FC(F)(F)C(O)=O.N1C=CC=CC=1C([O-])=O.[Ag+2].N1C=CC=CC=1C([O-])=O>[F:37][C:2]([F:36])([F:1])[C:3]1[CH:4]=[C:5]([C:13]2([C:32]([F:35])([F:34])[F:33])[CH2:17][CH2:16][N:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[CH:23]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])[CH2:22][CH2:21]4)[CH:14]2[OH:40])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Komponenten

8

Edukt 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 45377922N-[5-[3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl]indan-1-yl]propanamide

Produkt 1

HCID 89816262HCID 89816262, VerbindungAusbeute 5,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178524371HCID 178524371, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

131 mg (0.243 mmole) N-(5-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2,3-dihydro-1H-inden-1-yl)propanamide (Ex. No. (II-a-963), known from WO 2010/043315, Table 6, Ex. No. 273) was dissolved in a solution of 0.6 ml water, 6 ml acetonitrile and 1.2 ml trifluoroacetic acid. At 0° C. 86 mg (0.243 mmole) silver-(II)2-pyridinecarboxylate were added in small portions until the solution has been discoloured. Immediately after decolourization ethylacetate and sodium hydrogencarbonate solution were added. The aqueous solution was extracted additionally two times with ethylacetate. The combined extracts were dried and evaporated under reduced pressure. The residue was purified by a reversed phase chromatography with a gradient acetonitrile/water to obtain 9 mg (5.8%) of the title compound as a mixture of isomers. NMR data are given for the main isomer.

Aufarbeitung

  1. customAt 0° C
  2. extractionThe aqueous solution was extracted additionally two times with ethylacetate
  3. customThe combined extracts were dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by a reversed phase chromatography with a gradient acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-aff3313145be4865a6dddce188cf5f4a
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206122B2

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