2-Methylpentane → (R)-1-[(5-Methyl-isoxazol-3-ylcarbamoyl)-methyl]-3-(1-thiophen-2-yl cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192311
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:24][CH2:25][C:26]([NH:28][C:29]1[CH:33]=[C:32]([CH3:34])[O:31][N:30]=1)=[O:27].C(OCC)(=O)C.CCCC(C)C>C(#N)C>[Br-:24].[CH3:34][C:32]1[O:31][N:30]=[C:29]([NH:28][C:26]([CH2:25][N+:1]23[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:27])[CH:33]=1

Komponenten

6

Edukt 4

HCID 78922-MethylpentaneHCID 8857Ethyl AcetateHCID 64850652-Bromo-N-(5-methyl-isoxazol-3-yl)-acetamideHCID 58348375HCID 58348375, Verbindung

Produkt 1

HCID 44516988(R)-1-[(5-Methyl-isoxazol-3-ylcarbamoyl)-methyl]-3-(1-thiophen-2-yl cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromideAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Thiophen-2-yl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 5d) (68 mg) and 2-bromo-N-(5-methyl-isoxazol-3-yl)-acetamide (Example 6a) (45 mg) were dissolved in acetonitrile (2 mL) and stirred overnight. Ethyl acetate (10 mL) and isohexane (9 mL) were added and stirred overnight. The resulting crystals were filtered off and washed with ethyl acetate to afford the titled compound (82 mg).

Aufarbeitung

  1. stirringstirred overnight
  2. filtrationThe resulting crystals were filtered off
  3. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9b6781f2289446baa88bd09cf5bb0acd
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329729B2

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