N-[4-(2-Bromoacetyl)Phenyl]Acetamide → (R)-1-[2-(4-acetylamino-phenyl)-2-oxo-ethyl]-3-((R)-2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 1255070

Reaktionsgleichung

Reaktionsgleichung von HRID 1255070
[C:1]1([CH:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:39])[CH3:38])=[CH:32][CH:31]=1)=[O:29]>C(#N)C>[Br-:26].[C:37]([NH:36][C:33]1[CH:34]=[CH:35][C:30]([C:28](=[O:29])[CH2:27][N+:13]23[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]2)[C@@H:11]([O:10][C:8](=[O:9])[C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]3)=[CH:31][CH:32]=1)(=[O:39])[CH3:38]

Komponenten

4

Edukt 2

HCID 12364739N-[4-(2-Bromoacetyl)Phenyl]AcetamideHCID 46239457(R)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetate

Produkt 1

HCID 86643225(R)-1-[2-(4-acetylamino-phenyl)-2-oxo-ethyl]-3-((R)-2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (Diastereoisomer 1 of C2) (80.0 mg, 0.24 mmol) and N-(4-(2-bromoacetyl)phenyl)acetamide (60.9 mg, 0.24 mmol) in acetonitrile (2 mL) is heated in a microwave oven at 100° C. for 1 hour (UPLC-MS monitoring: complete conversion). The title compound is isolated by suction filtration and washed with Et2O (98.2 mg, 81% yield, off-white solid, bromide salt, single diastereoisomers).

Quellen und Nachweise

ORD-Eintrag
ord-ed4e821c78df44989f110d9ceed0bc5b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455646B2

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