Production of a special diphenylazetidinone derivative for use, e.g. as a cholesterol-reducing agent, involves acylation of an aminomethylphenyl-azetidinone compound with a long-chain mixed acid anhydride

• Main Authors: JUNKER, BERND, WOLLMANN, THEODOR ANDREAS, OTTO, BERNHARD, MAIER, CLAUS-JUERGEN
• Format: Patent
• Language: English; German
• Published: 02.06.2010
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

A method for the production of a 1-(p-aminomethylphenyl)-4-(p-methoxyphenyl)-3-[3'-(p-fluorophenyl)-3'-hydroxypropyl]-azetidin-2-one in which the amino group is acylated with a glucosylamidoundecanoyl group, involves reacting the glucosylamidoundecanoic acid with a carboxylic acid chloride and then reacting the resulting mixed acid anhydride with the unacylated amine. A method (M1) for the production of a 1-(p-aminomethylphenyl)-4-(p-methoxyphenyl)-3-[3'-(p-fluorophenyl)-3'-hydroxypropyl]-azetidin-2-one of formula (I), involves (a) reacting the compound of formula HOOC-(CH 2) 10-CONH-CH 2-(CHOH) 4-CH 2OH (II) with a compound of formula R 1-CO-Hal (III) to give a compound of formula R 1-CO-O-CO-(CH 2) 10-CONH-CH 2-(CHOH) 4-CH 2OH (IV) and then (b) reacting (IV) with a compound of formula (V) or its salts. Hal : Br, Cl or I; R 11-18C alkyl, in which one or more CH 2groups may be replaced by -O-, -CO-, -CH=CH-, -Ctriple boundC- or arylene and the alkyl groups may be substituted with one or more F, Cl, Br or I atoms. Independent claims are also included for (1) compounds of formula (IV) as above, and (2) a method (M2) for the production of the compound of formula (CH 3) 2CH-CH 2-OCOOCO-(CH 2) 10-CONH-CH 2-(CHOH) 4-CH 2OH (IVa) by reacting (II) with a compound of formula Hal-COO-isobutyl (IIIa). . [Image]. Die Erfindung betrifft ein verbessertes Verfahren zur Herstellung eines Diphenylazetidinons.