Morpholine → (R)-1-(2-(4-(morpholine-4-carbonyl)phenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 453699Notes

Reaction equation

HRID 453699 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Br-:13].[C:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:50])[CH2:24][N+:25]23[CH2:32][CH2:31][CH:28]([CH2:29][CH2:30]2)[C@@H:27]([O:33][C:34](=[O:49])[C@@H:35]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:26]3)=[CH:19][CH:18]=1)([OH:16])=O.[NH:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1>CN(C=O)C>[Br-:13].[N:51]1([C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:50])[CH2:24][N+:25]34[CH2:32][CH2:31][CH:28]([CH2:29][CH2:30]3)[C@@H:27]([O:33][C:34](=[O:49])[C@@H:35]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[NH:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:26]4)=[CH:19][CH:18]=2)=[O:16])[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 86660308HCID 86660308, compound

Product 1

HCID 86660309(R)-1-(2-(4-(morpholine-4-carbonyl)phenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromideYield 33.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1′-Carbonyldiimidazole (14.0 mg, 0.09 mmol) was added to a solution of (R)-1-(2-(4-carboxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (diastereomer 1 of C67) (50 mg, 0.09 mmol) in dry DMF (2 ml). The reaction mixture was stirred at room temperature for 2 hours. Then morpholine (7.52 mg, 0.09 mmol) was added, and the resulting reaction mixture was stirred at room temperature for 1 hour. DMF was evaporated and the crude was purified by preparative HPLC (eluents: CH3CN/H2O) to obtain (R)-1-(2-(4-(morpholine-4-carbonyl)phenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (18.9 mg, 33.8% yield).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at room temperature for 1 hour
  3. customDMF was evaporated
  4. customthe crude was purified by preparative HPLC (eluents: CH3CN/H2O)

Sources & evidence

ORD record
ord-2dbdf840f1f24ad9b4df57332d011011
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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