An asymmetric synthesis of L-[2-C-13]aspartic acid from sodium [2-C-13]acetate

Citation
K. Takatori et al., An asymmetric synthesis of L-[2-C-13]aspartic acid from sodium [2-C-13]acetate, J LABEL C R, 42(7), 1999, pp. 701-708
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Inorganic & Nuclear Chemistry
Journal title
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
ISSN journal
03624803 → ACNP
Volume
42
Issue
7
Year of publication
1999
Pages
701 - 708
Database
ISI
SICI code
0362-4803(199907)42:7<701:AASOLA>2.0.ZU;2-C
Abstract
L-[2-C-13]Aspartic acid was synthesized by using Dellaria's oxazinone label led with C-13 at the 3-position, prepared from phenyl [2-C-13]bromoacetate and (S)-2-phenylglycinol, as a chiral glycine equivalent. Phenyl [2-C-13]br omoacetate was derived from sodium [2-C-13]acetate. Alkylation of the [3-C- 13]oxazinone with ethyl bromoacetate was achieved with high diastereoselect ivity. Finally, sequential deprotection and removal of the chiral auxiliary of the alkylated [3-C-13]oxazinone afforded L-[2-C-13]aspartic acid.