2-Bromo-1-(thiophen-3-yl)ethan-1-one → HCID 54764990, Verbindung

HRID 469456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469456
[Br:1][CH2:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)=[O:4].[O:10]=[C:11]([O:29][C@@H:30]1[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1)[CH:12]([NH:19][C:20]1[CH:24]=[CH:23][S:22][C:21]=1[C:25]([O:27][CH3:28])=[O:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOC(C)=O>[Br-:1].[CH3:28][O:27][C:25]([C:21]1[S:22][CH:23]=[CH:24][C:20]=1[NH:19][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:11]([O:29][C@@H:30]1[CH:35]2[CH2:34][CH2:33][N+:32]([CH2:2][C:3](=[O:4])[C:5]3[CH:9]=[CH:8][S:7][CH:6]=3)([CH2:37][CH2:36]2)[CH2:31]1)=[O:10])=[O:26]

Komponenten

4

Edukt 2

HCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneHCID 46840422HCID 46840422, Verbindung

Produkt 1

HCID 54764990HCID 54764990, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Bromo-1-(thiophen-3-yl)ethanone (25.6 mg, 0.12 mmol) was added to a solution of methyl 3-(2-oxo-1-phenyl-2-((R)-quinuclidin-3-yloxy)ethylamino)thiophene-2-carboxylate (C11) (50 mg, 0.12 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight, and then the solvent was evaporated under vacuum. The residue was triturated with Et2O and then purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetoxy)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (44.3 mg, 58.6% yield).

Aufarbeitung

  1. customthe solvent was evaporated under vacuum
  2. customThe residue was triturated with Et2O
  3. custompurified by preparative HPLC (Eluent: CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-a175476e8e2149b3a8a1c891f352d0c6
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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