engleski

Useful Syntheses of 1'-Aminoferrocene-1-carboxylic Acid and Its Derivatives

In continuation of our studies in the field of ferrocene-containing amines, oligoamides and amino acids1 we decided to prepare and investigate some ferrocene heteroannularly substituted amino acids. This report is dealing with synthesis of the first ˛homologue˛ of this series - 1˘-aminoferrocene-1-carboxylic acid (5). Reaction of 1˘-methoxycarbonylferrocene-1-carboxylic acid with ethyl chloroformate/ triethylamine/ sodium azide gave methyl 1˘-azidocarbonylferrocene-1-carboxylate (1), which was rearranged in acetic anhidride and hydrolyzed into N-acetyl derivative 2. Azide 1 was converted into the corresponding benzyl carbamate 3, which was hydrolyzed into acid-carbamate 4 and hydrogenated into amino acid 5. The crucial intermediate 1 was transformed into tert-butyl carbamate 6 and hydrolyzed into N-Boc-derivative 7. By means of spectroscopic analysis and on the basis of other physical properties it was demonstrated that the amino acid prepared exists in the expected zwitterionic form. 1. Z. Zorić, V. Rapić, S. Lisac and M. Jukić, J. Polymer Sci., Part A: Polymer Chemistry 37 (1999) 25-36.

1'-Aminoferrocene-1-carboxylic Acid; N-acetyl derivative; N-Boc derivative

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