Original scientific paper

Synthetic Studies in the Chloramphenicol Series. III. Synthesis of threo-DL-Chloramphenicol from DL-Serine Ethyl Ether

D. Fleš ; Research Department, »Pliva" Pharmaceutical and Chemical Works, Zagreb, Croatia, Yugoslavia
B. Balenović ; Research Department, »Pliva" Pharmaceutical and Chemical Works, Zagreb, Croatia, Yugoslavia
R. Marušić ; Research Department, »Pliva" Pharmaceutical and Chemical Works, Zagreb, Croatia, Yugoslavia
N. Manger ; Research Department, »Pliva" Pharmaceutical and Chemical Works, Zagreb, Croatia, Yugoslavia

Abstract

A synthesis of threo-DL-chloramphenicol (I) from a-phthalimido-~-ethoxy-DL-propiophenone (II) is described. The crude ketone II obtained from a-phthalimido-~-ethoxy-DL-propionyl chloride via Friedel-Crafts reaction was reduced with aluminium isopropoxide to give a yield of 17.2 % of the corresponding carbinol III. This carbinol gave in a series of reactions threo -DL-chloramphenicol in an overall yield of 2.4 %.

Keywords

Hrčak ID:

249394

URI

https://hrcak.srce.hr/249394

Publication date:

1.5.1955.

Visits: 691 *