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Syntheses of [2-13C] and [1,2-13C] labelled α-ketoglutaric acid

✍ Scribed by Jack E. Baldwin; Robert M. Adlington; Mark A. Russell; Christopher J. Schofield; Mark E. Wood

Publisher
John Wiley and Sons
Year
1989
Tongue
French
Weight
353 KB
Volume
27
Category
Article
ISSN
0022-2135

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✦ Synopsis

The syntheses of a-ketoC2-' 3C]glutaric acid and a-ketoC1,2-' 'Cl glutaric acid were each achieved from commercial "CH,I in 5 steps. CH,NO,, prepared in situ from "CH,I and AgNO,, was treated with magnesium methyl carbonate, followed by acidified methanol to give 0,N13CH,C0,CH3. Michael addition to methyl acrylate, followed by in situ nitronate formation and ozonolysis gave the dimethyl ester of a-keto [Z-"C]glutaric acid, which was deprotected with hydrochloric acid. 02N''CH,'3C0,CH3 was prepared from "CH3N0, by reaction with aqueous KOH, followed by treatment with acidified methanol, and was converted t o 1,2-'3C-cr-ketoglutaric acid in a similar fashion to that used for mono-labelled material.

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