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A novel and efficient asymmetric synthesis of carbon-14 labeled (S,S)-2,7-di-boc-diamino[1,8-14C2]suberic acid

✍ Scribed by A. J. Villani; D. Saunders; A. Y. L. Shu; J. R. Heys

Publisher
John Wiley and Sons
Year
2002
Tongue
French
Weight
112 KB
Volume
45
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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