(R)-3-[2,2-Bis-(2-chloro-phenyl)-2-hydroxy-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide → (R)-3-[2-Hydroxy-2-(2-methoxy-phenyl)-2-phenyl-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2240323Notes

Reaction equation

[Br-:1].Cl[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1Cl)([OH:30])[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N+:15]([CH2:21][C:22](=[O:29])[NH:23][C:24]3[CH:28]=[CH:27][O:26][N:25]=3)([CH2:16][CH2:17]2)[CH2:14]1)=[O:11].[OH:38][C:39](C1C=CC=CC=1OC)(C1C=CC=CC=1)C(O)=O>>[Br-:1].[OH:30][C:9]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:38][CH3:39])([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:3]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N+:15]([CH2:21][C:22](=[O:29])[NH:23][C:24]3[CH:28]=[CH:27][O:26][N:25]=3)([CH2:16][CH2:17]2)[CH2:14]1)=[O:11]

Participants

Reactant 2

HCID 11534561(R)-3-[2,2-Bis-(2-chloro-phenyl)-2-hydroxy-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HCID 67538364Hydroxy-(2-methoxy-phenyl)-phenyl-acetic acid2×

Product 1

HCID 11671407(R)-3-[2-Hydroxy-2-(2-methoxy-phenyl)-2-phenyl-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

Procedure

This compound is prepared analogously to (R)-3-[2,2-bis-(2-chloro-phenyl)-2-hydroxy-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide [Example 1] by substituting bis-(2-chloro-phenyl)-hydroxy-acetic acid with Hydroxy-(2-methoxy-phenyl)-phenyl-acetic acid (Intermediate N).

Sources & evidence

ORD record: ord-2ceabfe5e1df47d88ac4c82e02780a7e
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723356B2

Reaction notes

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