The Improved Synthesis of OPC-29030, a Platelet Adhesion Inhibitor via Diastereoselective Oxidation of Chiral Non-racemic Sulfide.

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  • Matsugi Masato
    Department of Materials Chemistry, Graduate School of Engineering, Osaka University
  • Shimada Rieko
    Department of Materials Chemistry, Graduate School of Engineering, Osaka University
  • Ohata Shinji
    Department of Materials Chemistry, Graduate School of Engineering, Osaka University
  • Nojima Masatomo
    Department of Materials Chemistry & Frontier Research Center, Graduate School of Engineering, Osaka University
  • Fukuda Norio
    BPC Division, Second Tokushima Factory, Otsuka Pharmaceutical Co., Ltd.
  • Minamikawa Jun-ichi
    BPC Division, Second Tokushima Factory, Otsuka Pharmaceutical Co., Ltd.
  • Kita Yasuyuki
    Graduate School of Pharmaceutical Sciences, Osaka University

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  • Improved Synthesis of OPC 29030 a Platelet Adhesion Inhibitor via Diastereoselective Oxidation of Chiral Non racemic Sulfide

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Abstract

An improved synthetic route of OPC-29030, the platelet adhesion inhibitor, was established via the diastereoselective oxidation of a chiral non-racemic sulfide (R)-5 to (SS)-6 by the catalytic oxidation using VO(acac)2 and cumene hydroperoxide (CHP) in the presence of MS4A. Under the current condition, the diastereoselectivity was not influenced by the presence of moisture, and moderate to high selectivity (72% de) was obtained at −30 °C. The obtained sulfoxide, which diastereomeric excess was easily raised by the recrystallization, could successfully lead to OPC-29030.

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