Process for the preparation of tetronic acid derivatives

Details Process for the preparation of tetronic acid derivatives Process for the preparation of tetronic acid derivatives

C - Chemistry, Metallurgy

07

D

C07D 307/66 (2006.01) C07D 307/34 (2006.01)

Patent

CA 2211503

A process for the preparation of tetronic acid derivatives of the general formula: (see fig. I) in which R1 is hydroxyl or phenylamino and R2 is oxo or a group NR1. A 4-haloacetic acid ester is reacted with a base, the resulting tetronic acid intermediate is either diazotized or nitrosylated and the resulting tetronic acid derivative I is optionally reacted further with an amine hydrohalide. The resulting tetronic acid derivatives are important intermediates for the preparation of (+)-biotin, or of pharmaceutical or agricultural active compounds.

Un procédé pour la préparation de dérivés de l'acide tétronique de formule générale : (voir fig. I) où R1 est un groupe hydroxyle ou phénylamino et R2 est un oxo ou un groupe NR1. On fait réagir un ester de l'acide 4-haloacétique avec une base; l'intermédiaire de l'acide tétronique ainsi obtenu est soit diazoté soit nitrosylé, et on peut, facultativement, faire réagir davantage le dérivé I de l'acide tétronique obtenu avec un halohydrate d'amine. Les dérivés de l'acide tétronique obtenus sont d'importants intermédiaires pour la préparation de (+)-biotine ou de composés actifs dans les domaines de la pharmacologie ou de l'agriculture.

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