Helvetica Chimica Acta p. 1261 - 1267 (1987)
Update date:2022-07-29
Topics:
Datta, Subir
Hoesch, Lienhard
The 4-hydrazinobenzyl alcohol (3) was prepared (58percent) by diisobutylaluminiumhydride reduction of methyl 4-hydrazinobenzoate (4), whereas LiAlH4 of LiBH4 reduction of 4 proceeded further to yield (via intermediate 3) (4-tolylhydrazine (5).The alcohol 3 was stable under O2-free conditions and exhibited no tendency to eliminate H2O, neither thermally nor with H+ catalysis.Oxidation of 3 with SeO2 yielded 4-(hydroxymethyl)benzenediazonium ion (8), identified by its azo coupling product 9 with 2-naphthol.Condensation of 3 with 1-benzyl 5-hydrogen N-(benzyloxycarbonyl)-L-glutamate (1) in presence of dicyclohexylcarbodiimide afforded 82percent of N2-(benzyloxycarbonyl)-L-glutamic acid 1-(benzyl-ester) 5-(2-<4-(hydroxymethyl)phenyl>hydrazide) (11) which upon controlled hydrogenolysis (quinoline-sulfur-poisoned Pd/C catalyst) gave 82percent of L-glutamic acid 5-(2-<4-(hydroxymethyl)phenyl>hydrazide) (1), i.e. agaritine, a metabolite of Agaricus bisporus.Without poisoning of the catalyst, hydrogenolysis of (11) yielded L-glutamic acid 5-<2-(4-tolyl)hydrazide) (12).
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