Processes for producing azetidine-2-carboxylic acid and...

C - Chemistry – Metallurgy – 07 – D

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C07D 205/04 (2006.01)

Patent

CA 2287218

Efficient and economical processes for producing azetidine-2-carboxylic acid and intermediates thereof on an industrial scale. Azetidine-2-carboxylic acid of structural formula (5) is produced by reducing a 4-oxo-2- azetidinecarboxylic acid derivative of general formula (1) to form azetidine-2- methanol of structural formula (2), treating this compound with an amino- protecting agent to form an N-protected azetidine-2-methanol of general formula (3), treating this compound with an oxidizing agent to form an N- protected azetidine-2-carboxylic acid of general formula (4), and removing the amino-protecting group.

L'invention concerne des procédés efficaces et économiques permettant de préparer un acide azétidine-2-carboxylique et des intermédiaires de cet acide à l'échelle industrielle. Le procédé de préparation de l'acide azétidine-2-carboxylique représenté par la formule développée (5) ci-après consiste: à réduire un dérivé d'acide 4-oxo-2-azétidinecarboxylique de formule générale (1) pour former de l'azétidine-2-méthanol représenté par la formule développée (2) ci-après; à traiter ce composé par un agent amino-protecteur pour former un azétidine-2-méthanol à N protégé correspondant à la formule générale (3) ci-après; à traiter ce composé par un agent d'oxydation pour former l'acide azétidine-2-carboxylique à N protégé représenté par la formule générale (4) ci-après; et à supprimer le groupe amino-protecteur.

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