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

HRID 660091Notes

Reaction equation

HRID 660091 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:79])[NH:67][C:68]3[C:72]([C:73]4[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=4)=[CH:71][O:70][N:69]=3)([CH2:60][CH2:61]2)[CH2:58]1.[CH:80]1([C:86]([OH:96])([C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)[C:87](O)=[O:88])[CH2:85][CH2:84][CH2:83][CH2:82][CH2:81]1>>[Br-:1].[CH:90]1([C:86]([OH:96])([C:80]2[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=2)[C:87]([O:56][C@@H:57]2[CH:62]3[CH2:63][CH2:64][N+:59]([CH2:65][C:66](=[O:79])[NH:67][C:68]4[C:72]([C:73]5[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=5)=[CH:71][O:70][N:69]=4)([CH2:60][CH2:61]3)[CH2:58]2)=[O:88])[CH2:95][CH2:94][CH2:93][CH2:92][CH2:91]1

Participants

5

Reactant 4

HCID 97700(+-)-Cyclohexylphenylglycolic 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 86627865(R)-3-Hydroxy-1-[(4-phenyl-isoxazol-3-ylcarbamoyl)-methyl]-1-azonia-bicyclo[2.2.2]octane bromide2×

Product 1

HCID 11534632(R)-3-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-[(4-phenyl-isoxazol-3-ylcarbamoyl)-methyl]-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-[(4-phenyl-isoxazol-3-ylcarbamoyl)-methyl]-1-azonia-bicyclo[2.2.2]octane bromide (Intermediate I) and by replacing 2,2′-diphenylpropionic acid with cyclohexyl-hydroxy-phenyl-acetic acid, yielding the titled compound as a diastereomeric mixture. (M+ 544.4)

Sources & evidence

ORD record
ord-4ddc31da19984e8cae84e54dc0a70f66
Source dataset
uspto-grants-2011_12
Patent number
US08084463B2

Reaction notes

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