Original scientific paper

Synthesis of a-Amino-1-Adamantylacetic and a-Amino- 2-Adamantylacetic Acid

B. Gašpert ; Research Department »Pliva«, Pharmaceuticai and Chemicai Works, Zagreb, Croatia, Yugoslavia
S. Hromadko ; Research Department »Pliva«, Pharmaceuticai and Chemicai Works, Zagreb, Croatia, Yugoslavia
B. Vranešić ; Research Department »Pliva«, Pharmaceuticai and Chemicai Works, Zagreb, Croatia, Yugoslavia

Abstract

a-Amino-2-adamantylacetic acid (VII) was obtained when
2-adamantylcyanoacetylhydrazide (IX) was subjected to Curtius
rearrangement or 2-(2-adaman;tyl)-malonamic acid (XII) to Hofmann
degradation. The same amino acid was obtained when ri.-
bromo-2-adamantylacetic acid (VI) was •treated with ammonia.
Partial hydrolysis of diethyl adamantyl-(1)-malonate (XIV)
yie1ded ethyl adamantyl-(1)-malcmate (XV) which, after treatment
with thionyl chlodde and then ammonia, gave 2-(1-adamantyl)-
malonamic acid ethyl ester (XVII). Hofmann degradation of
2-(1 -adamantyl)-malonamic acid ethyl ester gave a-amino-1-
-adama:ntylacetic acid (XVIII).

Keywords

Hrčak ID:

196479

URI

https://hrcak.srce.hr/196479

Publication date:

30.4.1976.

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