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高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (4): 581-585.doi: 10.1007/s40242-016-6093-7

• Articles • 上一篇    下一篇

Efficient Synthesis of Beraprost Sodium

WANG Yue1, HOU Dalong2, LÜ Haoze2, ZHANG Baozhen2, WANG Ensi2   

  1. 1. Department of Thoracic Surgery of China-Japan Union Hospital of Jilin University, Changchun 130033, P. R. China;
    2. College of Pharmacy, Jilin University, Changchun 130021, P. R. China
  • 收稿日期:2016-03-14 修回日期:2016-04-28 出版日期:2016-08-01 发布日期:2016-05-30
  • 通讯作者: WANG Ensi E-mail:wangss@jlu.edu.cn
  • 基金资助:

    Supported by the Project of the Education Department of Jilin Province, China(No.2015535).

Efficient Synthesis of Beraprost Sodium

WANG Yue1, HOU Dalong2, LÜ Haoze2, ZHANG Baozhen2, WANG Ensi2   

  1. 1. Department of Thoracic Surgery of China-Japan Union Hospital of Jilin University, Changchun 130033, P. R. China;
    2. College of Pharmacy, Jilin University, Changchun 130021, P. R. China
  • Received:2016-03-14 Revised:2016-04-28 Online:2016-08-01 Published:2016-05-30
  • Contact: WANG Ensi E-mail:wangss@jlu.edu.cn
  • Supported by:

    Supported by the Project of the Education Department of Jilin Province, China(No.2015535).

摘要:

An efficient and straightforward synthesis of beraprost sodium was developed with dicyclopentadiene as a starting material, a one-pot reaction product 5 as key intermediate and the Prins reaction and the Horner-Wads- worth-Emmons reaction as key steps. The structures of the key intermediate and the target compound were confirmed by 1H NMR, 13C NMR and MS. The purity of beraprost sodium identified by high performance liquid chromatography(HPLC) was identical to that of Japanese Pharmacopoeia(16th). This development will be used for the industrial synthesis of beraprost sodium.

关键词: Beraprost sodium, One-pot reaction, Prins reaction, Horner-Wadsworth-Emmons reaction

Abstract:

An efficient and straightforward synthesis of beraprost sodium was developed with dicyclopentadiene as a starting material, a one-pot reaction product 5 as key intermediate and the Prins reaction and the Horner-Wads- worth-Emmons reaction as key steps. The structures of the key intermediate and the target compound were confirmed by 1H NMR, 13C NMR and MS. The purity of beraprost sodium identified by high performance liquid chromatography(HPLC) was identical to that of Japanese Pharmacopoeia(16th). This development will be used for the industrial synthesis of beraprost sodium.

Key words: Beraprost sodium, One-pot reaction, Prins reaction, Horner-Wadsworth-Emmons reaction