Solid supported synthesis of hydroxamic acids

C - Chemistry – Metallurgy – 07 – C

Patent

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Details

C07C 259/04 (2006.01) C07C 259/06 (2006.01) C07C 259/10 (2006.01) C07C 319/20 (2006.01) C07D 307/68 (2006.01) C07B 61/00 (2006.01) C07C 323/62 (2006.01)

Patent

CA 2318487

The subject invention involves processes for making hydroxamic acid compounds using a solid-support resin having an oxime moiety as the linking moiety of the resin, comprising the steps of (a) treating the resin with a carboxylic acid compound, such that it is attached to the resin by a condensation reaction between the oxime and carboxyl moieties; (b) optionally modifying the side chain; (c) cleaving a product from the resin by treating with O-tert- butyldimethylsilylhydroxylamine; (d) optionally modifying the side chain; and (e) optionally treating the resulting O-TBS-protected material with acid to produce an unprotected hydroxamic acid compound.

La présente invention concerne des processus permettant de fabriquer des composés d'acide hydroxamique au moyen d'une résine de support solide dans laquelle un fragment d'oxime constitue le fragment de liaison de cette résine. Les processus de cette invention consistent: a) à traiter ladite résine avec un composé d'acide carboxylique, de sorte que ce composé est lié à la résine par une réaction de condensation entre l'oxime et les fragments carboxyles; b) à modifier éventuellement la chaîne latérale; c) à dissocier un produit de la résine, grâce à un traitement à l'O-tert-butyldiméthylsilylhydroxylamine; d) à modifier éventuellement ladite chaîne latérale; et e) à traiter éventuellement la substance ainsi obtenue, protégée par O-TBS, à l'aide d'un acide, afin de produire un composé d'acide hydroxamique non protégé.

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