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An asymmetric synthesis of l ‐[3‐ 13 C]alanine
Author(s) -
Takatori Kazuhiko,
Toyama Sanae,
Narumi Shoko,
Fujii Seishiro,
Kajiwara Masahiro
Publication year - 2004
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.800
Subject(s) - chemistry , alkylation , methyl iodide , alanine , iodide , hydrolysis , chemical synthesis , enantioselective synthesis , stereochemistry , glycine , organic chemistry , medicinal chemistry , amino acid , catalysis , biochemistry , in vitro
l ‐[3‐ 13 C]Alanine was synthesized from [ 13 C]methyl iodide by using Dellaria's oxazinone, prepared from phenyl[2‐ 13 C]bromoacetate and ( S )‐2‐phenylglycinol, as a chiral glycine equivalent. Alkylation of the oxazinone with [ 13 C]methyl iodide was achieved with high diastereoselectivity. Hydrolysis and removal of the chiral auxiliary of the alkylated oxazinone gave l ‐[3‐ 13 C]alanine. Copyright © 2003 John Wiley & Sons, Ltd.