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Divergent synthesis of organophosphate [ 11 C]VX- and [ 11 C]Sarin-surrogates from a common set of starting materials

Divergent synthesis of organophosphate [ 11 C]VX- and [ 11 C]Sarin-surrogates from a common set of starting materials

Thomas R Hayes, Joseph E Blecha, Charles M Thompson, John M Gerdes, Henry F VanBrocklin

Appl Radiat Isot. 2019 Sep;151:182-186.

PMID: 31202183

Abstract:

Radiolabeled 1-[11C]ethyl, 4-nitrophenyl methylphosphonate (VX surrogate) and 2-[11C]-propanyl, 4-nitrophenyl methylphosphonate (sarin surrogate) were developed as organophosphate (OP) tracers. The [11C]ethyl- and [11C]isopropyl-iodide radiolabeled synthons were obtained by temperature controlled, in loop reactions of [11C]CO2 with MeMgBr followed by reduction with LiAlH4, then reaction with HI. Distillation of the [11C]alkyl iodides into a solution of hydrogen (4-nitrophenyl)methylphosphonate and cesium carbonate afforded the desired tracers in >95% radiochemical purity, yields from [11C]CO2 of 1-3% and 1.7-15.1 GBq/mmol molar activities.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AS212431	Isopropyl methylphosphonic acid-D7 solution			Price

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