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The 14 C, 13 C and 15 N syntheses of MON 37500, a sulfonylurea wheat herbicide
Author(s) -
Maxwell Brad D.,
Boyé Olivier G.,
Ohta Kazunari
Publication year - 2005
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.934
Subject(s) - chemistry , yield (engineering) , chloroacetic acid , ring (chemistry) , malonate , pyrimidine , diethyl malonate , sulfonylurea , ammonium , medicinal chemistry , imidazopyridine , pyridine , organic chemistry , stereochemistry , catalysis , medicine , materials science , insulin , metallurgy , endocrinology
[ 14 C] and [ 13 C]MON 37500 labeled in the imidazopyridine (Im) ring system were synthesized in seven steps in an overall yield of 39 and 28%, respectively, from [2‐ 14 C] and [2‐ 13 C]chloroacetic acid. [ 14 C]MON 37500 labeled in the pyrimidine (Pd) ring system was synthesized from [2‐ 14 C]diethyl malonate in four steps in 48% yield. Lastly, [ 15 N]MON 37500 was prepared in three steps in an overall yield of 28% from [ 15 N]ammonium chloride. Copyright © 2005 John Wiley & Sons, Ltd.