A first catalytic preparation of the popular antiplatelet drug (S)-clopidogrel, known with the tradename of Plavix, has been developed in a one-pot and innovative approach. The synthesis can be performed using commercially available ortho-chlorobenzaldehyde, 1-naphthylsulfonyl acetonitrile, tert-butyl hydroperoxide (TBHP), 4,5,6,7-tetrahydrothieno[3,2-c]pyridine and 20 mol % of a quinidine derived organocatalyst in a single solvent. A Knoevenagel/asymmetric epoxidation/domino ring-opening esterification (DROE) sequence enabled to obtain (S)-clopidogrel in 61 % overall yield and 62 % ee. Fine optimization of the reaction conditions proved to be crucial to set up a selective and efficient process.

One‐Pot Catalytic Synthesis of Optically Active Drug (S)‐Clopidogrel

Battaglia, Vincenzo
Methodology
;
Meninno, Sara
Methodology
;
Lattanzi, Alessandra
2023-01-01

Abstract

A first catalytic preparation of the popular antiplatelet drug (S)-clopidogrel, known with the tradename of Plavix, has been developed in a one-pot and innovative approach. The synthesis can be performed using commercially available ortho-chlorobenzaldehyde, 1-naphthylsulfonyl acetonitrile, tert-butyl hydroperoxide (TBHP), 4,5,6,7-tetrahydrothieno[3,2-c]pyridine and 20 mol % of a quinidine derived organocatalyst in a single solvent. A Knoevenagel/asymmetric epoxidation/domino ring-opening esterification (DROE) sequence enabled to obtain (S)-clopidogrel in 61 % overall yield and 62 % ee. Fine optimization of the reaction conditions proved to be crucial to set up a selective and efficient process.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4857437
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