The Synthesis Of Prasugrel Hydrochloride And Linezolid

The dissertation work includes two chapters.The chapter one is the synthesis of prasugrel hydrochloride. Prasugrel hydrochloride is an oral antiplatelet agent, which is primarily applied for the treatment of atherosclerosis and acute coronary syndrome. In this chapter prasugrel hydrochloride was synthesized from cyclopropyl-2-fluorobenzyl ketone and 5,6,7,7a-tetrahydro-4H-thieno [3,2-c]pyridine-one hydrochloride via bromination, condensation, acetylation and salt formation. The condition of the key condensation step was optimized and the yield of 60.4% was higher than the reported document. At last a novel route for the synthesis of prasugrel using 4,5,6,7-tetrahydrothieno[3,2-c]pyridine and a-cyclopropylcarbonyl-2--fluorobenzyl bromide as raw material via condensation and oxidation reaction was developed. The structure of prasugrel and its intermediates were identified by’H-NMR and its purity was measured by HPLC. The target compound was prepared in an overall yield of 37.7%.The chapter two is the synthesis of linezolid. Linezolid, belonged to oxazolidinone analogues, is a kind of novel structural and total synthetic antimicrobial agent. It is used in the treatment of diseases such us bacteremia, pneumonia and comprehensive infections of the skin, which has no cross-resistance taken with other antibacterials. In this chapter the synthetic routes of linezolid were reviewed. Linezolid had been synthesized through substitution, reduction, ring-opening, cyclization, Gabriel’s reaction, hydroammonolysis and acylation from raw material 3,4-difluoronitrobenzene and (R)-epichlorohydrin as chiral source. The present process without using azide was mild and very convenient to operate. The structure of linezolid and its intermediates were identified by ’H-NMR, Its polarimetry activity was also tested by rotation polarmetric analysis. The target compound was prepared in an overall yield of 24.3%.