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Synthesis of optically pure (D)‐phenyl[3‐ 14 C]alanine
Author(s) -
Koltai E.,
Alexin A.,
Rutkai Gy.,
Tóthsarudy É.
Publication year - 1998
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/(sici)1099-1344(1998110)41:11<977::aid-jlcr143>3.0.co;2-j
Subject(s) - chemistry , synthon , lithium aluminium hydride , bromide , hydrolysis , lithium (medication) , yield (engineering) , alanine , lithium hydride , aluminum hydride , benzyl bromide , lithium hydroxide , alkaline hydrolysis , hydroxide , benzyl alcohol , hydrochloric acid , medicinal chemistry , organic chemistry , amino acid , catalysis , ion , medicine , biochemistry , materials science , ion exchange , ionic bonding , metallurgy , endocrinology , methoxide
Lithium aluminium hydride reduction of methyl [7‐ 14 C]benzoate gave [7‐ 14 C]benzyl alcohol which was transformed (HBr, H 2 SO 4 ) to [7‐ 14 C]benzyl bromide. The latter was reacted with lithium N‐(bis‐methylthiomethylenimino)‐acetyl‐(2R)‐bornane‐10,2‐sultam (Oppolzer chiral synthon) followed by hydrochloric acid then lithium hydroxide hydrolysis and chromatography on a Dowex 50 column to give (D)‐phenyl[3‐ 14 C]alanine with 40% overall yield. The molar activity was higher than 50 mCi/mmol and e.e.>99% as measured by the Marfey method and a modified Marfey method with TLC scanning. The latter method is suitable for the measurement of the optical purity of any amino acid. Copyright © 1998 John Wiley & Sons, Ltd.