✦ LIBER ✦

Regioselective synthesis of (E)-2-[2H or 3H]-5-succinimido-4-oxo-pent-2-enoic acid

✍ Scribed by Arie L. Gutman; John B. Campbell

Publisher: John Wiley and Sons
Year: 1985
Tongue: French
Weight: 295 KB
Volume: 22
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580220703

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✦ Synopsis

Abstract

The synthesis of highly enriched C‐2 deuteriated and tritiated (E)‐5‐succinimido‐4‐oxo‐pent‐2‐enoic acid for use in enzymatic reduction is described. The starting materials 3‐methoxycarbonyl‐[3‐^2^H]propionyl chloride and 3‐methoxycarbonyl‐[3‐^3^H]propionyl chloride were prepared in high yield by regioselective deuteriation or tritiation of monomethyl succinate. The synthetic route involved regioselective bromination of 5‐succinimidolaevulinic acid followed by dehydrobromination.

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