Synthesis of Heliotramide
- 1 January 1959
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 12 (4) , 706-711
- https://doi.org/10.1071/ch9590706
Abstract
Both racemates of 4-methoxy-3-hydroxy-2-methylpentane-3-carboxamide are synthesized by reacting isopropylmagnesium chloride with 2-methoxypropionitrile, converting the resulting ketone into the cyanohydrin and hydrolysing to the amide. Comparison with heliotramide shows that the lower melting racemate, m.p. 81-82 �C, is (�)-heliotramide and thus of threo-configuration. The higher melting racemate, m.p. 145-146 �C, is the erythro-amide. Attempts to hydrolyse the amides to the carboxylic acids were unsuccessful. Heliotramide is prepared by heating heliotric acid with urea or by the usual acid chloride-ammonia procedure following protection of the hydroxyl group.Keywords
This publication has 0 references indexed in Scilit: