Thienamycin derivatives

Details Thienamycin derivatives Thienamycin derivatives

C - Chemistry, Metallurgy

07

D

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C07D 405/04 (2006.01) C07D 205/08 (2006.01) C07D 207/277 (2006.01) C07D 411/04 (2006.01) C07D 477/04 (2006.01) C07D 487/04 (2006.01)

Patent

CA 1191854

ABSTRACT OF THE DISCLOSURE Bicyclic compounds of the general formula (I), Image (I) wherein y1 and y2 represent a removable carbonyl protecting group, and Q is a Cl-5 alkyl group or a substituted benzyl group, are prepared in such a way that a) a compound of the ganaral formula (V), Image (V) wherein y1 and y2 are as defined above and R' is a removable amido protecting group othar than phenyl group, is activated on the carboxy group and then reacted with a salt of a malonic acid hemiestar, wherein the alcohol component is a Cl-5 aliphatic alcohol or a substituted benzyl alcohol, the resulting compound of the general formula (IV), Image (IV) wherein R', Q, yl and y2 are as defined above; is reacted with a sulfonic azide in the presence of a tertiary amine, or b) a compound of the general formula (V) is activat- ed on its carboxy group and reactad then with a diazoacatic acid ester, -2- thereafter the R' protecting group of a resulting compound of the general formula (III) Image (III) is removed, and the resulting compound of the general formula (II) Image (II) is subjected to ring closure to form the desired end-product.

418743

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