Preparing pentahydroxy-pentylcarbamoyl-undecanoic acid benzyl ester, useful to prepare tetrahydroxy-hexylcarbamoyl-undecanoic acid, comprises reacting dodecanedioic acid monobenzyl ester with halo-carbonyl compound and then with glucamine

摘要

Preparing 11-((2S,3R,4S)-2,3,4,5,5-pentahydroxy-pentylcarbamoyl)-undecanoic acid benzyl ester (I), comprises reacting dodecanedioic acid monobenzyl ester (IV) with a halo-carbonyl compound (VI) to obtain undecanoic acid benzyl ester of formula (V); and reacting (V) either with D-glucamine to give (I), or with (IV), followed by reacting (VIII) with D-glucamine to give (I). Preparing 11-((2S,3R,4S)-2,3,4,5,5-pentahydroxy-pentylcarbamoyl)-undecanoic acid benzyl ester (I), comprises reacting dodecanedioic acid monobenzyl ester (IV) with a halo-carbonyl compound of formula (Hal-C(=O)-R 1) (VI) to obtain undecanoic acid benzyl ester of formula (V); and reacting (V) either with D-glucamine to give (I), or with (IV) to bis(dodecanedioic acid monobenzyl ester) (VIII), followed by reacting (VIII) with D-glucamine to give (I). Hal : Br, Cl (preferred) or I; and R 11-18C-alkyl, in which one or more CH 2 groups are optionally substituted by O, CO, CH=CH, C?=C, or aryl or alkyl (optionally substituted by F, Cl, Br or I), preferably isobutyloxy, benzyloxy or tert.butyloxy (all preferred), CH 3, C 2H 5, propyl, isopropyl, butyl, isobutyl, tert.butyl, methyloxy, ethyloxy, propyloxy, isopropyloxy or butyloxy. Independent claims are included for: (1) 12-isobutoxycarbonyloxy-12-oxo-dodecanoic acid benzyl ester (Va); (2) the preparation of (Va) comprising reacting (IV) with a halo-carbonyl compound of formula (VIa); (3) bis(dodecanedioic acid monobenzyl ester) (VIII); and (4) the preparation of (VIII) comprising reacting (IV) with (VIa) to give (Va), and reacting (Va) with (IV). [Image].