Abstract

ORTIZ, Aurelio; ARELLANO, Omar; SANSINENEA, Estibaliz  and  BERNES, Sylvain. Stereoselective Crystallization as a Key Step for the Synthesis of New Epimers of Captopril Derivatives. J. Mex. Chem. Soc [online]. 2007, vol.51, n.4, pp.245-248. ISSN 1870-249X.

The present work describes the synthesis of two new diastereomers of captopril derivatives. These epimers were achieved by conjugate addition of thioacetic acid and α-toluenethiol to a α,β-unsaturated system. The diastereomeric ratios obtained from this reaction were low at 0 ^oC and moderate at -50 ^oC. The importance of this synthesis, however, is that in one case, both epimers can be isolated in good yields. Their isolation was possible because of the high crystallinity showed by one epimer compared to the other one. The absolute configuration of the solid compound was established by X-ray analysis.

Keywords : Captopril; ACE inhibitor; antihypertensive; conjugate addition of thiols.

        · abstract in Spanish     · text in English     · English ( pdf )