Heterocyclic carboxylic acids and a process for the...

C - Chemistry – Metallurgy – 07 – D

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260/335.5, 260/3

C07D 205/08 (2006.01) C07D 207/28 (2006.01) C07D 405/04 (2006.01) C07D 411/04 (2006.01)

Patent

CA 1189864

ABSTRACT OF THE DISCLOSURE New heterocyclic carbogylic acids of the general formula (I), (I) Image wherein y1 and y2 form together a removable carbonyl protecting group and R is a removable amido protecting group, are prepared in such a way that a compound of the gen- eral formula (IV), Image ( IV) wherein Z is a C1-5 alkyl group and R is as defined above, is reacted with a compound capable for the tem- porary protection of the carbonyl group, the resulting compound of the general formula (III), - 2 - Image (III) wherein R, Z, y1 and y2 are as defined above, is treated with an alkali metal halide, and the resulting compound of the general formula (II), Image (II) wherein Z, R, y1 and y2 are as defined above, is either hydrolysed selectively or separated into its isomers and the trans isomers is then hydrolysed. The resulting compounds of the general formula (I) are valuable intermediates of the synthesis of thienamycin and thienamycin analogues.

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