alpha-Cyclopentylmandelic acid → (R/S)-(2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoyl-methyl)-1-methyl-pyrrolidinium bromide

HRID 389919Notes

Reaction equation

HRID 389919 reaction equation
[Br-:1].[CH:2]1([C:8]([OH:33])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]([O:11][CH:12]2[CH2:16][CH2:15][CH2:14][N+:13]2([CH2:18][C:19](=[O:26])[NH:20][C:21]2[CH:25]=[CH:24][O:23][N:22]=2)[CH3:17])=[O:10])C[CH2:6][CH2:5][CH2:4][CH2:3]1.C1(C(C2C=CC=CC=2)(O)C(O)=O)CCCC1>>[Br-:1].[CH:2]1([C:8]([OH:33])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]([O:11][CH:12]2[CH2:16][CH2:15][CH2:14][N+:13]2([CH2:18][C:19](=[O:26])[NH:20][C:21]2[CH:25]=[CH:24][O:23][N:22]=2)[CH3:17])=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 98283alpha-Cyclopentylmandelic acidHCID 131730245(R/S)-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoyl-methyl)-1-methyl-pyrrolidinium bromide

Product 1

HCID 131730253(R/S)-(2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoyl-methyl)-1-methyl-pyrrolidinium bromide

Procedure

This compound is prepared by an analogous method to (1R/S,3R)-3((R/S)-(2-cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-pyrrolidinium bromide (QAX003) (Example 2) by replacing cyclohexyl-hydroxy-phenyl-acetic acid with cyclopentyl-mandelic acid.

Sources & evidence

ORD record
ord-b8f6ccb710b44ca5b1258338e033583e
Source dataset
uspto-grants-2013_02
Patent number
US08383625B2

Reaction notes

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