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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2240316Generated: November 3, 2026

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

https://huagongshe.com/reaction/2240316

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(+-)-Cyclohexylphenylglycolic acidHCID 97700—
Reactant(R)-3-(2-Cyclopentyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 11656809—
Reactant(R)-3-Hydroxy-1-(pyrazin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 86627863—
Reactant(R)-3-Hydroxy-1-(pyrimidin-4-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 86627870—
Product(R)-3-(2-Cyclohexyl-2-hydroxy-2-phenyl-acetoxy)-1-(pyrimidin-4-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 11584887—

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07723356B2
Source datasetuspto-grants-2010_05
ORD IDord-badf47d70e724dbd8c837f3149f0808a
Source noteuspto-grants-2010_05