Erythromycin. II. Des-N-methylerythromycin and N-Methyl-C14-erythromycin

EH Flynn, HW Murphy… - Journal of the American …, 1955 - ACS Publications
EH Flynn, HW Murphy, RE McMahon
Journal of the American Chemical Society, 1955ACS Publications
The reaction between erythromycin1 and ethyl chloroformate has been reported previously2
to yield the unexpected product,-dicarbethoxydes-N-methylerythromycin (II) in which a
methyl group has beendisplaced from the dimethylamino function originally present in
erythromycin. This in itself is a remarkable reaction. Most important, however, is the
possibility of using this reaction as a route to des-N-methylerythromycin (IV), which has
advantages as a subject for structural studies, for the preparation of C14-labeled erythro …
The reaction between erythromycin1 and ethyl chloroformate has been reported previously2 to yield the unexpected product,-dicarbethoxydes-N-methylerythromycin (II) in which a methyl group has beendisplaced from the dimethylamino function originally present in erythromycin. This in itself is a remarkable reaction. Most important, however, is the possibility of using this reaction as a route to des-N-methylerythromycin (IV), which has advantages as a subject for structural studies, for the preparation of C14-labeled erythro-mycin, and for study of the effect ofstructure on antibacterial activity. This paper reports the synthesis of 0, N-dicarbobenzoxydes-N-methyl-erythromycin, its conversion to des-N-methyl-erythromycin and reconversion of the latter to erythromycin (I) and to N-methyl-C14-erythromycin.
ACS Publications