Journal of Analytical Chemistry

, Volume 69, Issue 12, pp 1206–1213 | Cite as

Development and validation of HPLC method for the resolution of derivatives of 1-bromo-3-chloro-2-propanol: a novel chiral building block for the synthesis of pharmaceutically important compounds

  • Linga Banoth
  • Brahmam Pujala
  • Asit K. Chakraborti
  • Uttam Chand Banerjee
Articles
  • 96 Downloads

Abstract

The methods for the separation of racemic compounds [(RS)-1-bromo-3-chloro-2-propanol, (RS)-1-bromo-3-chloropropan-2-yl acetate] into the corresponding enantiomers were tried to develop in high performance liquid chromatography in a single injection mode. In the case of HPLC, both the reversed (Phenomenex Lux 5u cellulose-1, Lux 5u cellulose-2, Lux 5u amylose-1) and normal phase (Chiralcel OJH, ODH, ADH) chiral columns were used for this purpose. HPLC methods could not resolute the desired enantiomers. However, phenoxy derivatives of (RS)-1-bromo-3-chloro-2-propanol and (RS)-1-bromo-3-chloro- propan-2-yl acetate were separated by normal phase (ODH) column using a mobile phase consisting of n-hexane and isopropanol (80: 20) at a flow rate of 0.5 mL/min (25°C) and detected at 254 nm. The method was validated for linearity, range, accuracy and precision. The developed method was applied for monitoring the progress of lipase catalyzed enantioselective synthesis of (S)-1-bromo-3-chloropropan-2-yl acetate from (RS)-1-bromo-3-chloro-2-propanol. All the analytes were synthesized chemically.

Keywords

(RS)-1-bromo-3-chloro-2-propanol (RS)-1-bromo-3-chloropropan-2-yl acetate chiral HPLC ODH column 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Agustian, J., Kamaruddin, A.H., and Bhatia, S., Process Biochem., 2010, vol. 45, no. 10, p. 1587.CrossRefGoogle Scholar
  2. 2.
    Kuipers, W., Link, R., Standaar, P.J., Stoit, A.R., Van Wijngaarden, I., Leurs, R., and Ijzerman, A.P., Mol. Pharmacol., 1997, vol. 51, no. 5, p. 889.Google Scholar
  3. 3.
    Fegade, J.D., Chaudhari, R.Y., and Patil, V.R., Der Pharma Chemica, 2011, vol. 3, no. 2, p. 96.Google Scholar
  4. 4.
    Aubriot, S., Nicolle, E., Lattier, M., Morel, C., Cao, W., Daniel, K.W., Collins, S., Leclerc, G., and Faure, P., Bioorg. Med. Chem. Lett., 2002, vol. 12, no. 2, p. 209.CrossRefGoogle Scholar
  5. 5.
    Konkar, A.A., Zhu, Z., and Granneman, J.G., J. Pharmacol. Exp. Ther., 2000, vol. 294, no. 3, p. 923.Google Scholar
  6. 6.
    Cox, M.T., Jaggers, S.E., and Jones, G., J. Med. Chem., 1978, vol. 21, no. 2, p. 182.CrossRefGoogle Scholar
  7. 7.
    Narina, S.V. and Sudalai, A., Tetrahedron, 2007, vol. 63, no. 14, p. 3026.CrossRefGoogle Scholar
  8. 8.
    Das, B., Krishnaiah, M., and Venkateswarlu, K., Tetrahedron Lett., 2006, vol. 47, no. 26, p. 4457.CrossRefGoogle Scholar
  9. 9.
    Panchgalle, S.P., Gore, R.G., Chavan, S.P., and Kalkote, U.R., Tetrahedron: Asymmetry, 2009, vol. 20, no. 15, p. 1767.CrossRefGoogle Scholar
  10. 10.
    Gong, J.X., Shen, X., Yao, L.G., Jiang, H., Krohn, K., and Guo, Y.W., Org. Lett., 2007, vol. 9, no. 9, p. 1715.CrossRefGoogle Scholar
  11. 11.
    Kamal, A., Khanna, G., Krishnaji, T., and Ramu, R., Tetrahedron: Asymmetry, 2006, vol. 17, no. 8, p. 1281.CrossRefGoogle Scholar
  12. 12.
    Bredikhin, A.A., Bredikhina, Z.A., Zakharychev, D.V., and Pashagin, A.V., Tetrahedron: Asymmetry, 2007, vol. 18, no. 10, p. 1239.CrossRefGoogle Scholar
  13. 13.
    Choi, W.J. and Choi, C.Y., Biotechnol. Bioprocess Eng., 2005, vol. 10, no. 3, p. 1679.CrossRefGoogle Scholar
  14. 14.
    Kumar, P., Naidu, V., and Gupta, P., Tetrahedron, 2007, vol. 63, no. 13, p. 2745.CrossRefGoogle Scholar
  15. 15.
    Kim, M., Lim, I.T., Choi, G.B., Whang, S.Y., Ku, B.C., and Choi, J.Y., Bioorg. Med. Chem. Lett., 1996, vol. 6, no. 1, p. 71.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  • Linga Banoth
    • 1
  • Brahmam Pujala
    • 2
  • Asit K. Chakraborti
    • 2
  • Uttam Chand Banerjee
    • 1
  1. 1.Biocatalysis Laboratory, Department of Pharmaceutical TechnologyNational Institute of Pharmaceutical Education and Research Sector-67S. A. S. NagarIndia
  2. 2.Department of Medicinal ChemistryNational Institute of Pharmaceutical Education and Research Sector-67S. A. S. NagarIndia

Personalised recommendations