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A novel and efficient asymmetric synthesis of carbon‐14 labeled ( S , S )‐2,7‐di‐boc‐diamino[1,8‐ 14 C 2 ]suberic acid
Author(s) -
Villani A. J.,
Saunders D.,
Shu A. Y. L.,
Heys J. R.
Publication year - 2002
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.534
Subject(s) - chemistry , strecker amino acid synthesis , diastereomer , enantiomer , hydrolysis , asymmetric carbon , acylation , nitrile , organic chemistry , chiral auxiliary , carbon fibers , enantiomeric excess , chiral derivatizing agent , hydrochloric acid , enantioselective synthesis , medicinal chemistry , chiral column chromatography , catalysis , optically active , materials science , composite number , composite material
Five hundred mCi of Potassium [ 14 C]cyanide at a specific activity of 51 mCi/mmol was used to diastereoselectively introduce the carbon‐14 label into 1,6‐hexanedial via a thermodynamically controlled asymmetric Strecker reaction using ( R )‐(‐)‐2‐phenylglycinol as the chiral auxiliary. The expected and predominant ( R , S / S , R ) diastereomer ( 2 ) was separated by preparative normal phase HPLC. The chiral auxiliary was removed by oxidation with lead tetraacetate and the resulting benzylimino nitrile exhaustively hydrolyzed in hydrochloric acid to give ( S , S )‐2,7‐diamino[1,8‐ 14 C 2 ]suberic acid ( 6 ). Subsequent acylation with di‐tert‐butyldicarbonate gave the title compound ( 1 ) with a radiochemical purity of 95.5%, a specific activity of 113 mCi/mmol, and an enantiomeric purity of 95.5% e.e. To our knowledge this is the first report of the asymmetric Strecker methodology being applied to the synthesis of a carbon‐14 labeled amino acid. Copyright © 2002 John Wiley & Sons, Ltd.