Process for producing penam compound

Details Process for producing penam compound Process for producing penam compound

C - Chemistry, Metallurgy

07

D

C07D 499/04 (2006.01) C07B 53/00 (2006.01)

Patent

CA 2584128

An industrially advantageous process for efficiently producing a 2.alpha.- methyl-2.beta.-[(1,2,3-triazol-1-yl)methyl]penam-3.alpha.~carboxylic acid ester as the target compound while significantly inhibiting an undesirable cepham compound from generating as a by-product. Diphenylmethyl 2.beta.- bromomethyl-2.alpha.-methylpenam-3.alpha.-carboxylate (BMPB) is reacted with 1,2,3-triazole in a halogenated hydrocarbon at -5~C or lower. By conducting the reaction in a halogenated hydrocarbon at -5~C or lower, the generation of an undesirable cepham compound as a by-product can be significantly inhibited, whereby the target diphenylmethyl 2.alpha.-methyl-2.beta.-[(1,2,3-triazol-1- yl)methyl]penam-3.alpha.~carboxylate (TMPB) can be efficiently produced.

La présente invention a pour objet un procédé avantageux sur le plan industriel qui permet de synthétiser de façon efficace un ester d~acide 2.alpha.-méthyl-2.beta.-[(1,2,3-triazol-1-yl)méthyl]péname-3.alpha.­-carboxylique au titre de composé cible, tout en inhibant de façon significative la formation d~un dérivé de céphame au titre de sous-produit. Une réaction entre le 2.beta.-bromométhyl-2.alpha.-méthylpéname-3.alpha.-carboxylate de diphénylméthyle (BMPB) et le 1,2,3-triazole est menée dans un hydrocarbure halogéné à une température inférieure ou égale à -5 °C. En menant la réaction dans un hydrocarbure halogéné à une température inférieure ou égale à -5 °C, il est possible d~inhiber de façon significative la génération d~un dérivé de céphame non désiré, tout en synthétisant de façon efficace le 2.alpha.-méthyl-2.beta.-[(1,2,3-triazol-1-yl)méthyl]péname-3.alpha.­-carboxylate de diphénylméthyle (TMPB) attendu.

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