Premium
Regioselective synthesis of (E)‐2‐[ 2 H or 3 H]‐5‐succinimido‐4‐oxo‐pent‐2‐enoic acid
Author(s) -
Gutman Arie L.,
Campbell John B.
Publication year - 1985
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580220703
Subject(s) - regioselectivity , chemistry , halogenation , yield (engineering) , chloride , medicinal chemistry , tritium , organic chemistry , catalysis , materials science , metallurgy , physics , nuclear physics
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.