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Synthesis of CHMPA-D

Authors: Peech Reddy PhD, Huahua Jian PhD, Isil Dilek PhD, Ryan Carrell, Ning Chang PhD, Uma Sreenivasan PhD
Presented at NMEC, August 2009

Phosphorus compounds containing the P-C bond are not particularly abundant in nature but they have diverse biological activity and have attracted considerable synthetic and pharmacological interest. Aside from beneficial applications, they are used in the production of chemical warfare agents (CWAs) such as soman (GD), tabun (GA), sarin (GB) and cyclosarin (GF).

Many of these agents are prone to hydrolysis to produce the corresponding O-alkyl hydrogen alkylphosphonates. These hydrolyzed products are persistent in the environment and provide good evidence of the specific agent used and produced. Stable isotope labeled derivatives of O-alkyl hydrogen alkylphosphonates are useful in detection and quantitation of CWAs.

We will present the synthesis of cyclohexyl trideuteromethylphosphonic acid, a breakdown product of cyclosarin, and analytical data related to deuterium/hydrogen exchange. Synthesis by the traditional route used for the native analog afforded labeled cyclohexyl trideuteromethylphosphonic acid that was developed to obtain isotopically pure cyclohexyl trideuteromethylphosphonic acid. LCMS and GCMS were used to track exchange and isotopic purity.

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