Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
A Synthesis of DL-Tryptophan from Acrolein
Itsutoshi MaedaRyonosuke Yoshida
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1968 Volume 41 Issue 12 Pages 2975-2978

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Abstract

DL-Tryptophan hydrantoin was obtained from phenylhydrazone of β-(hydanto-5-yl)-propionaldehyde acetal (5-(γ,γ-dialkoxypropyl)hydantoin) by Fischer’s indole synthesis. β-(Hydanto-5-yl)propionaldehyde acetal was prepared by Bucherer’s reaction from 1,1-diacetoxy-4,4-dialkoxybutane obtained by the hydroformylation of acrolein acetate. Attempts to crystallize β-(hydanto-5-yl)-propionaldehyde acetal from Bucherer’s reaction solution were unsuccessful, but 5-alkoxy-1,3-dioxoperhydropyrro[1,2-c]imidazole was obtained by treating the solution with ion exchange resins in alcohol. It could be also converted to tryptophan hydantoin.

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