Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Synthesis, Resolution and Configuration of β-Hydroxyvaline
Jun-ichi Oh-hashiKaoru Harada
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1966 Volume 39 Issue 10 Pages 2287-2289

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Abstract

DL-β-Hydroxyvaline was synthesized from sodium β,β-dimethylglycidate by aminolysis with benzylamine, followed by hydrogenolysis. N-Benzoyl-DL-β-hydroxyvaline was resolved by use of (−)-α-methylbenzylamine to yield (−)-N-benzoyl-β-hydroxyvaline. The configuration of VI was determined by converting it to methyl N-benzoyl-β-chlorovalinate (I) and subsequent hydrogenolysis of I yielded (−)methyl N-benzoylvalinate (II). From II, optically pure D-(−)-valine was obtained upon hydrolysis.

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