Original scientific paper

Attempted Diastereoselective Preparation and Chiroptical Properties of (2S)-1-(3-Mercapto-2-Methyl-1-Oxopropyl)-L-Proline (Captopril) and Some Congeners

G. Snatzke ; Chair for Structural Chemistry, Ruhr University, D-4630 Bochum, FR Germany
E. Decorte ; CRC - Compagnia di Ricerca Chimica SpA, 1-33048 San Giovanni al Natisone (UD), Italy
T. Kovač ; CRC - Compagnia di Ricerca Chimica SpA, 1-33048 San Giovanni al Natisone (UD), Italy
F. Moimas ; CRC - Compagnia di Ricerca Chimica SpA, 1-33048 San Giovanni al Natisone (UD), Italy
L. Habuš ; "Ruđer Bošković" Institute, P.O. Box 1016, YU-41001 Zagreb, Croatia, Yugoslavia
V. Šunjić ; "Ruđer Bošković" Institute, P.O. Box 1016, YU-41001 Zagreb, Croatia, Yugoslavia

Abstract

CD and 13C-NMRstudy of the eonformational properties of (2S)-1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline (captopril, 1), and its congeners 2-5, 8, 9 is reported. 13C-NMRdata (in DMSO-d6) reveal an E/Z (cis/trans) ratio of ea. (15-30) : (70-85) for the N-acetyl-prolines 1, 5, 10, and for N-acetyl-L-proline. CD data indicate practically identical conformations for the ring systems of 8 and 9. Attempted diastereoselective cyclization of the sodium salt of 7 or the free thioacid into 8 and 9 resulted in low chemical yields (-30%) and low diastereoselectivity, favouring formation of the »wrong- diastereomer 9 in small excess (-20%).

Keywords

Hrčak ID:

175499

URI

https://hrcak.srce.hr/175499

Publication date:

10.8.1989.

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