C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 207/416 (2006.01) C07C 303/22 (2006.01) C07C 309/17 (2006.01)
Patent
CA 2303929
The salt of a sulfonated succinic acid is cyclized, then converted to novel sulfonated hydroxamic acids by reaction with hydroxylamine (which is added or formed in situ), and the novel hydroxamic acid is then cyclized to the sulfo-N- hydroxysuccinimide salt. Novel sulfo-hydroxamic acid intermediates are formed during this procedure. A process of forming a sulfo-N-hydroxysuccinimide by cyclizing a sulfohydroxamic acid is also described. Alternatively, the present invention describes a novel method for the synthesis of sulfo-N- hydroxysuccinimide salts in which commercially available sulfosuccinic acid salt in an aqueous medium is heated in the presence of an alcohol to form a diester of the succinic acid sulfonate. The diester is then reacted with hydroxylamine (e.g., from the hydrochloride salt) (e.g., in an alkaline buffered aqueous environment, e.g., at room temperature) to form the sulfo-N- hydroxysuccinimide. This is an extremely simple and direct process that does not produce a significant level of irremovable impurities.
L'invention concerne la cyclisation d'un sel d'acide succinique sulfoné, puis sa conversion en acide hydroxamique sulfoné de type nouveau par réaction avec une hydroxylamine (par adjonction ou formation in situ); ce nouvel acide est ensuite cyclisé en sel sulfo-N-hydroxysuccinimide. Le processus donne de nouveaux intermédiaires d'acide sulfo-hydroxamique. L'invention concerne également un procédé relatif à la fabrication de sulfo-N-hydroxysuccinimide par cyclisation d'acide sulfo-hydroxamique. A titre de variante, on décrit un procédé de synthèse pour les sels sulfo-N-hydroxysuccinimide, qui consiste à chauffer dans un milieu aqueux un sel d'acide sulfo-succinique du commerce, en présence d'un alcool, pour former un diester du sulfonate d'acide succinique. Ensuite, on fait réagir le diester avec une hydroxylamine (par exemple, d'un sel du type chlorhydrate), par exemple dans un environnement aqueux à tamponnage alcalin, et par exemple à température ambiante, de manière à obtenir le sulfo-N-hydroxysuccinimide. Il s'agit d'un procédé extrêmement simple et direct qui ne donne aucun niveau important d'impuretés non éliminables.
Bremmer Martin Lee
Wilkes Marty Carey
Bremmer Martin Lee
Gowling Lafleur Henderson Llp
Pierce Chemical Company
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