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An improved procedure for the synthesis of DL‐[2‐ 13 C]‐glutamic acid
Author(s) -
Potrzebowski Marek J.,
Stolowich Neal J.,
Ian Scott A.
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.2580280312
Subject(s) - chemistry , yield (engineering) , methyl acrylate , adduct , catalysis , glutamic acid , guanidine , michael reaction , organic chemistry , amino acid , polymer , copolymer , biochemistry , materials science , metallurgy
A convenient two‐step chemical synthesis of DL‐[2‐ 13 C]‐glutamic acid from methyl acrylate and diethyl acetamidomalonate is described. Synthesis of the Michael adduct (III) was effected in quantitative yield by employing strong amino bases as catalysts. The reactivities of three such catalysts, tetramethyl guanidine (TMG), 1,8‐diazobicyclo [5,4,0]‐undec‐7‐ene (1,5‐5) (DBU) and 1,5‐diazobicyclo [4,3,0] non‐5‐ene (DBN) were compared by 13 C NMR and all are shown to catalyse the reaction quantitatively, however at markedly different rates.