CRCU

Chemical Research in Chinese Universities ›› 2011, Vol. 27 ›› Issue (2): 224-227.

• Articles • Previous Articles     Next Articles

Novel Method for Selective Debenzylation Under Maintenance of Fluoro Atom Substituted on β-Amino Acids

ZHENG Yi1, WU Gang2, ZHU Xin-rong2, LI Yue-jie2, MA Yu-heng2, ZHAO Xin2, LU Tao1* and ZHU Yong-qiang2*   

  1. 1. School of Basic Sciences, China Pharmaceutical University, Nanjing 210009, P. R. China;
    2. Jiangsu Key Laboratory of Molecular Targeted Antitumor Drug Research, Jiangsu Simcere Pharmaceutical Research Institute, Nanjing 210042, P. R. China
  • Received:2010-05-21 Revised:2010-10-15 Online:2011-03-25 Published:2011-03-09
  • Contact: LU Tao and ZHU Yong-qiang E-mail:lutao@cpu.edu.cn; zhyqscu@hotmail.com
  • Supported by:

    Supported by the National Key New Drug Creation Program of China(No.2009ZX09103-001) and the Jiangsu Key Laboratory of Molecular Targeted Antitumor Drug Research Foundation, China(No.BM2008201).

PDF (PC)

Abstract: tert-Butyl (R)-3-amino-3-(3-fluorophenyl)propanoate(5) was prepared with conventional debenzylation method. However, the tert-butyl (R)-3-[(S)-1-phenylethyl-amino]-3-(3-fluorophenyl) propanoate(6) and tert-butyl (R)-3-amino-3-phenylpropanoate(7) were generated as the byproducts under the general catalytic hydrogenation Pd(OH)2/C-H2 conditions. So a series of experiments was performed to optimize the reaction conditions so that product 5 could be obtained with high purity and yield. Finally an effective catalytic system, Pd/C-HCOOH-CH3OH, was discovered.

Key words: β-Amino acid, Debenzylation, Defluorination, Catalytic hydrogenation