Processes of producing glutamic acid compounds and...

C - Chemistry – Metallurgy – 07 – C

Patent

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C07C 229/36 (2006.01) A23L 1/236 (2006.01) A23L 2/60 (2006.01) C07C 51/353 (2006.01) C07C 51/38 (2006.01) C07C 59/285 (2006.01) C07C 59/347 (2006.01) C07C 59/48 (2006.01) C07C 227/08 (2006.01) C07C 229/24 (2006.01) C07C 251/36 (2006.01) C07D 209/08 (2006.01) C07D 209/20 (2006.01)

Patent

CA 2471847

A process for preparing industrially and efficiently glutamic acid compounds (such as monatin) useful as sweeteners or intermediates for the production of drugs or the like; a process for preparation of intermediates used therein; novel intermediates included among them; a process for preparation of optically active monatin; a process for preparation of intermediates used therein; and novel intermediates included among them. Specifically, a process for the preparation of glutamic acid compounds (or salts thereof) including monatin, which comprises preparing a ketoglutaric acid compound serving as a precursor of the objective glutamic acid compound by condensing a specific pyruvic acid compound with oxalacetic acid or pyruvic acid through cross-aldol reaction and, if necessary, subjecting the obtained condensate to decarboxylation, and replacing the carbonyl group of the ketoglutaric acid compound by an amino group.

L'invention concerne un procédé industriel efficace de préparation de composés d'acide glutamique (tels que la monatine), utilisés comme édulcorants, ou de leurs intermédiaires, servant dans la production de médicaments ou analogues. L'invention concerne également un procédé de préparation d'intermédiaires utilisés dans ledit procédé; de nouveaux intermédiaires présents parmi lesdits intermédiaires; un procédé de préparation de monatine active optiquement; un procédé de préparation d'intermédiaires utilisés dans ledit procédé; et de nouveaux intermédiaires présents parmi lesdits intermédiaires. L'invention concerne en particulier un procédé de préparation de composés d'acide glutamique (ou de sels de ceux-ci), notamment de monatine. Ce procédé consiste à préparer un composé d'acide cétoglutarique servant de précurseur au composé d'acide glutamique visé, par condensation d'un composé d'acide pyruvique spécifique avec un acide oxalacétique ou un acide pyvurique, par l'intermédiaire d'une réaction d'aldolisation croisée ; si besoin est, à soumettre le condensat obtenu à une décarboxylation; et à remplacer le groupe carbonyle du composé d'acide cétoglutarique par un groupe amino.

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