3-(Chloromethyl)-5-(3-methoxyphenyl)-1,2,4-oxadiazole → (R)-1-((5-(3-methoxyphenyl)-1,2,4-oxadiazol-3-yl)methyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride
Reaction equation
[Cl:1][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[O:5][N:4]=1.[C:16]1([C@@H:22]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:23]([O:25][C@@H:26]2[CH:31]3[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]3)[CH2:27]2)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[Cl-:1].[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][N+:28]34[CH2:29][CH2:30][CH:31]([CH2:32][CH2:33]3)[C@@H:26]([O:25][C:23](=[O:24])[C@@H:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:27]4)[N:7]=2)[CH:13]=[CH:12][CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(Chloromethyl)-5-(3-methoxyphenyl)-1,2,4-oxadiazole (33.4 mg, 0.15 mmol) was added to a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (50.0 mg, 0.15 mmol) in acetonitrile (2 ml). The reaction was stirred at room temperature overnight. The solvent was evaporated, and the resulting solid was triturated with Et2O (2 ml) to obtain (R)-1-((5-(3-methoxyphenyl)-1,2,4-oxadiazol-3-yl)methyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride (82.3 mg, 99% yield).
Workup
- customThe solvent was evaporated
- customthe resulting solid was triturated with Et2O (2 ml)
Sources & evidence
- ORD record
- ord-3aa2ceff19984d8ba5890d258ac1c072
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563577B2
Reaction notes
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