Preparation of [4s- (4.alpha., 7.alpha., 10a.beta.)]-4-...

Details Preparation of [4s- (4.alpha., 7.alpha., 10a.beta.)]-4-... Preparation of [4s- (4.alpha., 7.alpha., 10a.beta.)]-4-...

C - Chemistry, Metallurgy

07

D

C07D 513/04 (2006.01)

Patent

CA 2366390

N-protected-L-homocysteine disulfide of the formula see Formula I or an activated form thereof is reacted with (S)-2-amino- 6,6-dimethoxyhexanoic acid, methyl ester to give the disulfide intermediate of the formula see Formula II The disulfide intermediate of formula II is reacted to cleave the disulfide bond and the resulting monomer is subjected to an acid catalyzed cyclization reaction to give the N-protected lactam of the formula Image Removal of the N-protecting group gives [4S- (4.alpha., 7.alpha., 10.alpha..beta.)] 1 -4-aminooctahydro-5-oxo-7H- pyrido[2,1-b] [1,3]thiazepine-7-carboxylic acid, methyl ester which along with its salt is useful as an intermediate in the preparation of the dual inhibitor [4S-(4.alpha.(R*),7.alpha.,10.alpha..beta.]] -octahydro-4-[(2-mercapto-1-oxo- 3-phenylpropyl)amino] -5-oxo-7H-pyrido-]2,1- b] [1,3]thiazepine-7-carboxylic acid. -61-

Selon l'invention, un disulfure de L-homocystéine de formule (I), dont l'azote est protégé, ou une forme activée de ce composé, est mis en réaction avec l'ester méthylique de l'acide (S)-2-amino-6,6-diméthoxyhexanoïque afin d'obtenir le disulfure intermédiaire de formule (II). Ce disulfure est mis à réagir pour scinder la liaison disulfure et le monomère qui en résulte est soumis à une réaction de cyclisation à catalyse acide afin de donner le lactame de formule, dont l'azote est protégé. L'enlèvement du groupe protecteur de l'azote donne l'ester méthylique de l'acide [4S-(4 alpha ,7 alpha ,10a beta )]-4-amino-octahydro-5-oxo-7H-pyrido[2,1-b][1,3]thiazépine-7-carboxylique, qui avec ses sels est un intermédiaire utile dans la préparation de l'inhibiteur dual, l'acide [4S-[4 alpha (R*),7 alpha ,10a beta ]]-octahydro-4-[(2-mercapto-1-oxo-3-phénylpropyl)amino]-5-oxo-7H-pyrido[2,1-b][1,3]thiazépine-7-carboxylique.

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