alpha-Cyclopentylmandelic acid → (R)-3-(2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2240315Notes

Reaction equation

HRID 2240315 reaction equation
[Br-:1].C1(C(C2C=CC=CC=2)(C)C(O[C@@H]2C3CC[N+](CC(=O)NC4C=CON=4)(CC3)C2)=O)C=CC=CC=1.[Br-].O[C@@H]1C2CC[N+](CC(=O)NC3C=CON=3)(CC2)C1.[Br-].[OH:56][C@@H:57]1[CH:62]2[CH2:63][CH2:64][N+:59]([CH2:65][C:66](=[O:74])[NH:67][C:68]3[CH:73]=[N:72][CH:71]=[CH:70][N:69]=3)([CH2:60][CH2:61]2)[CH2:58]1.[CH:75]1([C:80]([OH:90])([C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=2)[C:81](O)=[O:82])[CH2:79][CH2:78][CH2:77][CH2:76]1>>[Br-:1].[CH:75]1([C:80]([OH:90])([C:84]2[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=2)[C:81]([O:56][C@@H:57]2[CH:62]3[CH2:63][CH2:64][N+:59]([CH2:65][C:66](=[O:74])[NH:67][C:68]4[CH:73]=[N:72][CH:71]=[CH:70][N:69]=4)([CH2:60][CH2:61]3)[CH2:58]2)=[O:82])[CH2:79][CH2:78][CH2:77][CH2:76]1

Participants

5

Reactant 4

HCID 98283alpha-Cyclopentylmandelic acidHCID 11678278(R)-3-(2,2-Diphenyl-propionyloxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 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 11656809(R)-3-(2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

Procedure

This compound is prepared analogously to (R)-3-(2,2-Diphenyl-propionyloxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide (Example 4), substituting (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 by replacing 2,2′-diphenylpropionic acid with cyclopentyl-hydroxy-phenyl-acetic acid, yielding the titled compound as a diastereomeric mixture. (M+465.4)

Sources & evidence

ORD record
ord-89412e9432074ad88b9eeb93d1421f97
Source dataset
uspto-grants-2010_05
Patent number
US07723356B2

Reaction notes

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