Plavix - Clopidogrel sulfate

Optically pure a- and P-hydroxy esters have frequently been employed as convenient intermediates for the preparation of complex molecules. In particular, these motifs are present in a number of natural products. Among them, methyl (R)-mandelate [(R)-la] and methyl (R)-o-chloromandelate [(R)-lb] are valuable syn-thons (Scheme 4.2). la is used as an intermediate for the synthesis of several pharmaceuticals and lb is a building block for the antithrombotic agent, (S)-clopidogrel, commercialized under the brand name Plavix (clopidogrel sulfate). 

USAN Clopidogrel sulfate Trade Name Plavix Sanofi/Bristol-Myers Sqibb Launched 1993 M.W. 321.8... 

Plavix (Clopidogrel hydrogen sulfate). Bristol-Myers Squibb Phannaceuticals Ltd. UK Sum-maty of prcduct characteristics, June 2007... 

Clopidogrel (SR 25990) (Plavix Sanofi-Aventis) is the hydrogen sulfate salt of the S enanthiomer of methyl 2-(2-chlorophenyl)-2-[4,5,6,7-tetrahydrothieno(3,4-c)pyridine-5-yl] acetate. Its molecular formula is CI6HI6CIN02S, H2S04 (molecular weight of 419.9) (Fig. 2). 

Clopidogrel (12) is marketed by Sanofi-Synthlebo and BMS as the hydrogen sulfate salt under the trade name Plavix. It is a platelet aggregation inhibitor that is used as an antithrombotic agent for the reduction of cardiovascular events. The synthesis is straightforward (Scheme 31.8).102 107 The asymmetry is obtained by a classical resolution.103 It is possible to recycle the undesired isomer.108... 

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