An improved process for preparing simvastatin

Details An improved process for preparing simvastatin An improved process for preparing simvastatin

C - Chemistry, Metallurgy

07

D

C07D 309/30 (2006.01)

Patent

CA 2438477

The present invention relates to an improved process for preparing simvastatin and more particularly, the improved process for preparing simvastatin expressed by formula 1 with high yield and high purity by performing the following sequential processes comprising: (i) hydrolysis of lovastatin as starting material with potassium t-butoxide in an organic solvent and small amount of water under a mild reaction condition, followed by lactonization of the obtained solid intermediate with preventing from formation of by-products; (ii) protection of an alcohol group with t-butyldimethylsilyl group which can be easily removed with concentrated hydrochloric acid without the formation of by-products; (iii) acylation of the obtained protected intermediate with acyloxytriphenyl phosphonium salt as an acylating agent under a mild reaction condition; and (iv) removal of the silyl protective group with a concentrated hydrochloric acid. The present invention is to provide the improved process of preparing simvastatin expressed by formula 1 environmentally sound, economically efficient, and industrially useful.

La présente invention concerne un procédé amélioré de préparation de la simvastatine et, plus particulièrement, de simvastatine représentée par la formule 1, à fort rendement et pour une pureté élevée. Ce processus englobe les opérations suivantes: (i) hydrolyse de lovastatine avec du potassium t-butoxyde dans un solvant organique et une petite quantité d'eau en conditions de réaction douces, suivie d'une lactonisation du produit intermédiaire solide ainsi obtenu tout en empêchant la formation de produits secondaires; (ii) protection d'un groupe alcool avec un groupe t-butyldimethylsilyl pouvant être extrait facilement avec de l'acide chlorhydrique concentré sans formation de produits secondaires; (iii) acylation de l'intermédiaire ainsi obtenu avec un sel d'acyloxytriphényl phosphonium comme agent d'acylation en conditions de réaction douces; et (iv) extraction du groupe silyle protecteur au moyen d'acide chlorhydrique concentré. Cette invention concerne un processus amélioré de préparation de simvastatine représentée par la formule 1, ceci de manière rationnelle au plan écologique et utile au plan industriel.

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