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A Robust HPLC Method for Easily Oxidizable Phosphine Ligand Analysis.

Lauren Weisel¹, Liam Corcoran², Steve Castro¹

¹Analytical Research & Development, Merck Sharp & Dohme LLC (MSD), Rahway, NJ 07065, USA.

Journal of Chromatographic Science

|February 24, 2023

Summary

Analysis of phosphine ligands using high-performance liquid chromatography (HPLC) is challenging due to oxidation. A new HPLC method using tris(2-carboxyethyl)phosphine (TCEP) effectively prevents on-column degradation, improving accuracy and sensitivity for phosphine ligand analysis.

Keywords:

XPhos high performance liquid chromatography method development on-column oxidation phosphines

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Area of Science:

Analytical Chemistry
Organic Chemistry
Pharmaceutical Analysis

Background:

Phosphine ligands are crucial in synthesizing active pharmaceutical ingredients via transition-metal-catalyzed cross-coupling reactions.
Chromatographic analysis of phosphine ligands is hindered by their susceptibility to oxidation, leading to inaccurate results.

Purpose of the Study:

To investigate the cause of out-of-specification (OOS) results in XPhos raw material analysis using high-performance liquid chromatography (HPLC).
To develop an improved HPLC method for the accurate and sensitive analysis of phosphine ligands.

Main Methods:

An out-of-specification (OOS) investigation was conducted on XPhos raw material using HPLC.
A modified HPLC method was developed by adding a trace amount of tris(2-carboxyethyl)phosphine (TCEP) to the aqueous mobile phase.
The modified method aimed to passivate the LC column and prevent on-column degradation/oxidation.

Main Results:

On-column degradation/oxidation was identified as the cause of OOS results in the original HPLC method.
The addition of TCEP to the mobile phase effectively prevented on-column degradation and oxidation of phosphine ligands.
The modified HPLC method demonstrated significantly improved robustness, precision, and sensitivity.

Conclusions:

On-column degradation is a significant challenge in the HPLC analysis of phosphine ligands.
Adding a trace amount of TCEP to the mobile phase is a general and effective strategy to mitigate on-column degradation and oxidation.
This approach enhances the reliability and performance of HPLC methods for analyzing phosphine ligands and related compounds.