Original scientific paper

On the Configuration of β-Amino-d-Methyl Hexanoic Acid (β-Aminohomoleucine)

D. Keglević-Brovet ; Chemical Institute, Faculty of Science, University of Zagreb, and Tracer Laboratory, Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia

Abstract

The configuration of (+)-B-amino-d-methyl hexanoic acid (B -aminohomoleucine) (Ila), obtained by the application of the Arndt-Eistert synthesis on L- leucine (I) was determined. B-Phthalimidoil-d- methyl hexanoyl chloride (III) was converted via Rosenmund-Zetsche reaction into the corresponding aldehyde IV and ethylene mercaptal V. Raney nickel reduction of V gave ( + )-4-phthalimido-2-methyl- hexane (VI). Hydrolysis of VI with hydrobromic acid yielded (-) - 4-amino-2 -methyl-hexane hydrobromide (VII) . The compounds VI and VII were also obtained from 1-diazo-3-phthalimido-5-methyl hexan-2-one (VIII) by a different way, Wolff rearrangement being not applied. VIII was converted to the corresponding ketone (IX), resp. thioketal (X), which was desulphurized to VI. The compounds VI and VII, obtained by both ways, had the same signs of rotation.

Keywords

Hrčak ID:

245621

URI

https://hrcak.srce.hr/245621

Publication date:

25.3.1958.

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