(R)-3-[2-Hydroxy-2-(4-methoxy-phenyl)-2-phenyl-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide → (R)-3-(2-Hydroxy-2-phenyl-2-o-tolyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2240322Notes

Reaction equation

HRID 2240322 reaction equation
[Br-:1].[OH:2][C:3]([C:30]1[CH:35]=[CH:34][C:33](OC)=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:4]([O:6][C@@H:7]1[CH:12]2[CH2:13][CH2:14][N+:9]([CH2:15][C:16](=[O:23])[NH:17][C:18]3[CH:22]=[CH:21][O:20][N:19]=3)([CH2:10][CH2:11]2)[CH2:8]1)=[O:5].N12CCC(CC1)[C@@H](OC(=O)C(O)(C1C=CC(OC)=CC=1)C1C=CC=CC=1)[CH2:39]2.N12CCC(CC1)[C@@H](OC(=O)C(O)(C1C=CC=CC=1)C1C=CC=CC=1C)C2>>[Br-:1].[OH:2][C:3]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:39])[C:4]([O:6][C@@H:7]1[CH:12]2[CH2:11][CH2:10][N+:9]([CH2:15][C:16](=[O:23])[NH:17][C:18]3[CH:22]=[CH:21][O:20][N:19]=3)([CH2:14][CH2:13]2)[CH2:8]1)=[O:5]

Participants

4

Reactant 3

HCID 11671405(R)-3-[2-Hydroxy-2-(4-methoxy-phenyl)-2-phenyl-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 86627868Hydroxy-(4-methoxy-phenyl)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 86627869Hydroxy-phenyl-o-tolyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester2×

Product 1

HCID 11656930(R)-3-(2-Hydroxy-2-phenyl-2-o-tolyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

Procedure

This compound is prepared using an method analogous to (R)-3-[2-hydroxy-2-(4-methoxy-phenyl)-2-phenyl-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]-octane bromide (Example 22) by replacing hydroxy-(4-methoxy-phenyl)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Intermediate O) with hydroxy-phenyl-o-tolyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Intermediate P).

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-98e1f22b7ed64a68a431a751b1169d30
Source dataset
uspto-grants-2010_05
Patent number
US07723356B2

Reaction notes

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