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Synthesis of deuterium labelled analogs of fluazifop and haloxyfop
Author(s) -
Bartels Michael J.,
Gatling Sterling C.
Publication year - 1990
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.2580280214
Subject(s) - chemistry , deuterium , trifluoromethyl , ring (chemistry) , molecule , stereochemistry , hydrogen–deuterium exchange , medicinal chemistry , organic chemistry , hydrogen , alkyl , physics , quantum mechanics
Synthetic routes have been described for the preparation of stable isotope‐labelled analogs of two aryloxyphenoxypropionates, each containing approximately four deuterium atoms in the central phenyl ring of the molecule. Fluazifop‐2′,3′,5′,6′‐ 2 H 4 [2‐(4‐((5‐(trifluoromethyl)‐2‐pyridinyl)‐oxy)phenoxy)propionic acid‐2′,3′,5′,6′‐ 2 H 4 ] and haloxyfop‐2′,3′,5′,6′‐ 2 H 4 [2‐(4‐((3‐chloro‐5‐(trifluoromethyl)‐2‐pyridinyl)oxy)phenoxy)propionic acid‐2′,3′,5′,6′‐ 2 H 4 ] were synthesized from the common intermediate HPPA‐2′,3′,5′,6′‐ 2 H 4 [2‐(4‐hydroxyphenoxy)propionic acid‐2′,3′,5′,6′‐ 2 H 4 ]. This intermediate was obtained from HPPA via acid‐catalyzed deuterium exchange ( 2 H 2 SO 4 in 2 H 2 O and CH 3 O 2 H).