Original scientific paper

Ferrocene Compounds. XXIX.* Efficient Syntheses of 1’-Aminoferrocene-1-carboxylic Acid Derivatives

Lidija Barišić ; Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia
Vladimir Rapić ; Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia
Veronika Kovač ; Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia

Abstract

The syntheses of 1'-aminoferrocene-1-carboxylic acid (2a) and its derivatives are reported. Reaction of 1'-methoxycarbonylferrocene-1-carboxylic acid with ethyl chloroformate / triethylamine / sodium azide gave methyl 1'-azidocarbonylferrocene-1-carboxylate (4), which was rearranged in acetic anhydride and hydrolyzed into N-acetyl derivative of 2a. Azide 4 was converted into the corresponding benzyl carbamate 7, which was hydrolyzed into acid-carbamate 9 and hydrogenated into amino acid 2a. The crucial in-termediate 4 was transformed into tert-butyl carbamate 10 and hydrolyzed into N-Boc-2a.

Keywords

ferrocene; 1'-aminoferrocene-1-carboxylic acid; C-protected derivatives of; N-protected derivatives of

Hrčak ID:

127496

URI

https://hrcak.srce.hr/127496

Publication date:

4.2.2002.

Visits: 2.167 *