A process for the preparation of .beta.-lactam derivatives

Details A process for the preparation of .beta.-lactam derivatives A process for the preparation of .beta.-lactam derivatives

C - Chemistry, Metallurgy

07

D

C07D 501/00 (2006.01) C12P 35/02 (2006.01)

Patent

CA 2374686

A process for the preparation of Cefuroxime acid (I), which comprises the following steps: (1) Extraction of deacetyl 7-glutaryl ACA (II) aqueous solution at acid pH with organic solvents (for example according to the procedures disclosed in US 5,801,241); (2) drying the resulting solution while preventing lactonization of the intermediate; (3) carbamoylation of the hydroxymethyl group at the 3- position by reaction with chlorosulfonyl isocyanate or similar products; (7) extraction of the carbamoyl derivative from step 3 with water at neutral pH; (8) enzymatic hydrolysis of the amide at the 7- position of the cephalosporanic ring with glutaryl acylase; (6) acylation of the amino group by condensation with 2-furanyl(sin- methoxyimino)acetic acid chloride or mixed anhydride.

L'invention concerne un procédé pour la préparation d'acide céfuroxime selon la formule (I). Ce procédé comprend les étapes suivantes :(1) Extraction de déacétyle 7-glutaryle ACA à un pH acide avec des solvants organiques ( par exemple selon les procédures décrites dans le brevet US 5,801,241); (2) séchage de la solution obtenue tout en évitant la lactonisation du produit intermédiaire; (3) carbamoylation du groupe hydroxyméthyle à la position 3 par réaction du chlorosulfonyle isocyanate ou de produits similaires; (7) extraction du dérivé de carbamoyle obtenu à l'étape 3 avec de l'eau à un pH neutre; (8) hydrolyse enzymatique de l'amide à la position 7 de la chaîne céphalosporanique avec du glutaryle acylase; (6) acylation du groupe aminé par condensation avec du chlorure d'acide furanyl(sin-méthoxyimino)acétique ou de l'anhydride mélangé.

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