14-chlorodaunomycin and process for the preparation of...

C - Chemistry – Metallurgy – 07 – H

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260/208.1

C07H 15/252 (2006.01)

Patent

CA 1303027

ABSTRACT OF THE DISCLOSURE A new compound, i.e., 14-chlorodaunomycin, and its method of preparation are provided. The new compound, useful as an antitumor agent and as an intermediate in the preparation of (2"R)-4'-0-tetrahydropyranyladriamycin, is obtained by reaction of daunomycin with an alkyl orotho-formate and a brominating agent to produce a 14-bromo-13- dialkylketaldaunomycin, hydrolysis of the latter compound, then adding an excess of a solid metal/chloride to produce an acid addition salt of 14-chlorodaunomycin and concurrently salting out the latter compound from the reaction solution, followed by recovering the 14-chlorodaunomycin acid addition salt.

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