a. Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of

Chapter 23, Problem 23.57

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a. Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. The racemic drug can be prepared from the racemic -halo ester by the following reaction. What is the structure of clopidogrel? Cl Cl CO2CH3 K2CO3 clopidogrel (racemic) NH S + b. A single enantiomer of clopidogrel can be prepared in three steps from the chiral -hydroxy acid A. Identify B and C in the following reaction sequence, and designate the confi guration of the enantiomer formed by this route as R or S. Cl HO NH S clopidogrel H2SO4 (single enantiomer) CH3OH pyridine TsCl A B C H COOH

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