C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 233/84 (2006.01)
Patent
CA 2143419
The invention relates to a novel process for the preparation of ergothioneine. The process for the chemical synthesis of the different optical forms of ergothioneine is characterized in that it essentially comprises steps which consist in preparing or using an N .alpha.,N .alpha.-dimethy- lated histidine ester salt (optically active if necessary), treating this compound with an alkyl, alkenyl or aryl halogenothionoformate in the presence of a base, protecting the sulfur-containing substituent in the compound obtained, converting this protected compound to a compound of the trimethylammonium type and freeing the desired ergothioneine by saponification or acid hydrolysis, as appropriate. This process affords a better yield and ensures an excellent optical purity.
L'invention concerne un nouveau procédé de préparation de l'ergothionéine. Le procédé de synthèse chimique des différentes formes optiques de l'ergothionéine est caractérisé en ce qu'il comprend essentiellement les étapes consistant à préparer ou utiliser un sel d'ester d'histidine N alpha ,N alpha -diméthylée, si nécessaire optiquement actif; à traiter ce composé, par un halogénothionoformiate d'alkyle, d'alkényle ou d'aryle, en présence d'une base; et après protection du substituant soufré du composé obtenu, transformer ce dernier en un composé de type triméthylammonium; et à libérer l'ergothionéine désirée par saponification ou hydrolyse acide, selon le cas. Ce procédé procure un meilleur rendement et assure une excellente pureté optique.
Xu Jinzhu
Yadan Jean-Claude
Bioxytech
Norton Rose Or S.e.n.c.r.l. S.r.l./llp
Oxis Isle Of Man Limited
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