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Synthesis of 2‐(bromomethyl‐ 13 C)‐fumaric acid (bromomesaconic acid)
Author(s) -
Aberhart D. John,
Hsu ChiTung
Publication year - 1981
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.2580180708
Subject(s) - chemistry , fumaric acid , trifluoroacetic acid , isomerization , acetylene , medicinal chemistry , propionates , organic chemistry , catalysis
The fumarase inhibitor, bromomescaconic acid, has been synthesized with 13 C labeling in the bromomethyl group. Di‐t‐butyl acetylene‐dicarboxylate was converted with Li ( 13 CH 3 ) 2 Cu to di‐t‐butyl (methyl‐ 13 C)citraconate. Photochemical isomerization of this to di‐t‐butyl (methyl‐ 13 C)mesaconate, followed by deblocking with trifluoroacetic acid gave the title compound.