4-(2-bromoacetyl)benzoic Acid → HCID 86660308, compound

HRID 453698Notes

Reaction equation

HRID 453698 reaction equation
[C:1]1([C@@H: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:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=1)=[O:29]>CCOC(C)=O>[Br-:26].[C:34]([C:33]1[CH:37]=[CH:38][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)([OH:36])=[O:35]

Participants

4

Reactant 2

HCID 27568364-(2-bromoacetyl)benzoic AcidHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

Product 1

HCID 86660308HCID 86660308, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (300 mg, 0.89 mmol) in EtOAc (5 ml), was added 4-(2-bromoacetyl)benzoic acid (238 mg, 0.98 mmol), and the reaction was stirred at r.t. for 15 hours. The precipitate was collected by suction filtration to obtain (R)-1-(2-(4-carboxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (500 mg, 97% yield).

Workup

  1. filtrationThe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-c9bc1c9d01614947b4468fcca7451642
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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