(+-)-Cyclohexylphenylglycolic acid → (R)-3-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrimidin-4-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 660090Notes

Reaction equation

HRID 660090 reaction equation
[Br-:1].C1(C(O)(C2C=CC=CC=2)C(O[C@@H]2C3CC[N+](CC(=O)NC4C=NC=CN=4)(CC3)C2)=O)CCCC1.[Br-].O[C@@H]1C2CC[N+](CC(=O)NC3C=NC=CN=3)(CC2)C1.[Br-].[OH:57][C@@H:58]1[CH:63]2[CH2:64][CH2:65][N+:60]([CH2:66][C:67](=[O:75])[NH:68][C:69]3[CH:74]=[CH:73][N:72]=[CH:71][N:70]=3)([CH2:61][CH2:62]2)[CH2:59]1.[CH:76]1([C:82]([OH:92])([C:86]2[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=2)[C:83](O)=[O:84])[CH2:81][CH2:80][CH2:79][CH2:78][CH2:77]1>>[Br-:1].[CH:86]1([C:82]([OH:92])([C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=2)[C:83]([O:57][C@@H:58]2[CH:63]3[CH2:64][CH2:65][N+:60]([CH2:66][C:67](=[O:75])[NH:68][C:69]4[CH:74]=[CH:73][N:72]=[CH:71][N:70]=4)([CH2:61][CH2:62]3)[CH2:59]2)=[O:84])[CH2:91][CH2:90][CH2:89][CH2:88][CH2:87]1

Participants

5

Reactant 4

HCID 97700(+-)-Cyclohexylphenylglycolic acidHCID 11656809(R)-3-(2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 86627863(R)-3-Hydroxy-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 86627870(R)-3-Hydroxy-1-(pyrimidin-4-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide2×

Product 1

HCID 11584887(R)-3-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrimidin-4-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

Procedure

This compound is prepared analogously to (R)-3-(2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide (Example 15) by replacing (R)-3-Hydroxy-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo-[2.2.2]octane bromide (Intermediate H) with (R)-3-Hydroxy-1-(pyrimidin-4-ylcarbamoyl-methyl)-1-azonia-bicyclo[2.2.2]octane bromide (Intermediate Q) and by replacing cyclopentyl-hydroxy-phenyl-acetic acid with cyclohexyl-hydroxy-phenyl-acetic acid, yielding the titled compound as a diastereomeric mixture. (M+ 479.5).

Sources & evidence

ORD record
ord-4f11bf07be744137a49bf783ba3cfd77
Source dataset
uspto-grants-2011_12
Patent number
US08084463B2

Reaction notes

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