Process for preparation of .alpha.-hydroxycarboxylic acid...

Details Process for preparation of .alpha.-hydroxycarboxylic acid... Process for preparation of .alpha.-hydroxycarboxylic acid...

C - Chemistry, Metallurgy

07

C

C07C 231/02 (2006.01) C07C 235/34 (2006.01)

Patent

CA 2461438

The invention concerns a novel process for the preparation of 2-phenyl-2- hydroxy-N-[2-(3-alkoxy-4-hydroxyphenyl)-ethyl]-acetamides of the formula (I), wherein R1 is alkyl, R2 and R3 are each independently hydrogen or alkyl, and R4 is optionally substituted aryl or optionally substituted heteroaryl, which process comprises reacting a 2-(3-alkoxy-4-hydroxyphenyl)-ethylamine of the formula (II), wherein R1 R2 and R3 are as defined above with a .alpha.- hydoxycarboxylic acid ester of the formula (III) or a dioxolanone of the formula (III)a, wherein R4 is as defined above, and R5, R6 and R7 independently of each other are lower alkyl. The compounds of formula (I) are important intermediates for a novel group of fungicides derived from mandelic acid amides.

L'invention concerne un nouveau procédé de préparation de 2-phényl-2-hydroxy-N-[2-(3-alkoxy-4-hydroxyphényl)-éthyl]-acétamides représentés par la formule I dans laquelle R?1¿ est alkyle, R?2¿ et R?3¿ sont indépendamment chacun hydrogène ou alkyle, et R?4¿ est aryle ou hétéroaryle à substitution facultative. Ce procédé consiste à faire réagir un 2-(3-alkoxy-4-hydroxyphényl)-éthylamine représenté par la formule II dans laquelle R?1¿, R?2¿ et R?3¿ sont tels que définis ci-dessus avec un ester d'acide hydroxycarboxylique-.alpha. représenté par la formule III ou un dioxolanone représenté par la formule IIIa dans laquelle R?4¿ est tel que défini ci-dessus, et R?5¿, R?6¿ et R?7¿ sont indépendamment chacun un alkyle inférieur. Les composés de la formule I sont des intermédiaires importants pour un nouveau groupe de fongicides issus des amides d'acide mandélique.

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