(+-)-Cyclohexylphenylglycolic acid → (R)-3-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 660093Notes

Reaction equation

HRID 660093 reaction equation
[Br-:1].O[C@@H]1C2CC[N+](CC(=O)NC3C=CON=3)(CC2)C1.[Br-].[OH:21][C@@H:22]1[CH:27]2[CH2:28][CH2:29][N+:24]([CH2:30][C:31](=[O:39])[NH:32][C:33]3[CH:38]=[N:37][CH:36]=[CH:35][N:34]=3)([CH2:25][CH2:26]2)[CH2:23]1.[CH:40]1([C:46]([OH:56])([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:47](O)=[O:48])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>>[Br-:1].[CH:50]1([C:46]([OH:56])([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:47]([O:21][C@@H:22]2[CH:27]3[CH2:28][CH2:29][N+:24]([CH2:30][C:31](=[O:39])[NH:32][C:33]4[CH:38]=[N:37][CH:36]=[CH:35][N:34]=4)([CH2:25][CH2:26]3)[CH2:23]2)=[O:48])[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]1

Participants

4

Reactant 3

HCID 97700(+-)-Cyclohexylphenylglycolic acidHCID 86627857(R)-3-Hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 86627863(R)-3-Hydroxy-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide2×

Product 1

HCID 11548573(R)-3-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

Procedure

This compound is prepared as a diastereomeric mixture using an method analogous to Example 4, by replacing (R)-3-hydroxy-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide (Intermediate A) with (R)-3-Hydroxy-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide (Intermediate H) and 2,2′-diphenylpropionic acid with cyclohexyl-hydroxy-phenyl-acetic acid.

Workup

  1. customThis compound is prepared as a diastereomeric mixture

Sources & evidence

ORD record
ord-15da2dc414724f52ad2d24f1034203eb
Source dataset
uspto-grants-2011_12
Patent number
US08084463B2

Reaction notes

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