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Synthesis of α,β-DI[3H]–2–fluoro–L–histidine

✍ Scribed by Kazuyuki Takahashi; Kenneth L. Kirk; Louis A. Cohen

Publisher
John Wiley and Sons
Year
1986
Tongue
French
Weight
315 KB
Volume
23
Category
Article
ISSN
0022-2135

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✦ Synopsis

The potent antimetabolite, 2-fluoro-L-hi~tidine~ has been synthesized from 2-f luoroimidazole with nonexchangeable 3H labeling in the side chain. 2-Fluoro-4-iodoimidazole was N-tritylated, was subjected to metal-halogen exchange with n-butyllithium, and the carbanion formylated with DMF. The imidazole-4-aldehyde was condensed with hippuric acid, the azlactone WEB solvolyzed with methanol, and the trityl group was removed by selective reduction with PtS2. The resulting 2-fluoro-a-benzamidoacryllc ester was reduced with tritium gas and the blocking groups were removed successively with base and with acylase I to produce the L-enantiomer of the free amino acid analogue.

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