Biocatalytic synthesis of (S)-Practolol, a selective
β-blocker

• Authors: Sachin Mulik , Saptarshi Ghosh , Jayeeta Bhaumik , Uttam C. Banerjee
• Languages of publication: EN

Abstracts

EN

The present study describes an efficient
chemoenzymatic synthesis of enantiopure (S)-Practolol,
a selective β-adrenergic receptor blocker. Prior to
the synthesis of the target, a synthetic protocol for
(RS)-N-4-(3-chloro-2-hydroxypropoxy)phenylacetamide,
an essential precursor, was developed. Various commercial
lipases were screened for the kinetic resolution of (RS)-
N-4-(3-chloro-2-hydroxypropoxy)phenylacetamide using
toluene as solvent and vinyl acetate as an acyl donor.
Among various lipases screened, Pseudomonas cepacia
sol-gel AK showed the highest enantioselectivity (96%
enantiomeric excess with 50% conversion), affording
(S)-1-(4-acetamidophenoxy)-3-chloropropan-2-yl acetate.
Optimization of the reaction parameters was carried
out in order to find the best-suited conditions for the
biocatalysis. Furthermore, the enantiopure intermediate
was hydrolyzed and the resulting product was reacted with
isopropylamine to afford (S)-Practolol. This biocatalytic
procedure depicts a green technology for the synthesis of
(S)-Practolol with better yield and enantiomeric excess.

Keywords

EN

enantiopure; lipase; chemoenzymatic; enantioselectivity; biocatalysis

• Publisher: De Gruyter Open
• Journal: Biocatalysis
• Year: 2014
• Volume: 1
• Issue: 1

Dates

received

13 - 5 - 2015

online

20 - 1 - 2016

accepted

28 - 9 - 2015

Contributors

author

Sachin Mulik

• Department of
  Pharmaceutical Technology (Biotechnology), National Institute
  of Pharmaceutical Education and Research, Sector-67,,S. A. S.
  Nagar-160062, Punjab

author

Saptarshi Ghosh

• Department of
  Pharmaceutical Technology (Biotechnology), National Institute
  of Pharmaceutical Education and Research, Sector-67,,S. A. S.
  Nagar-160062, Punjab

author

Jayeeta Bhaumik

• Department of
  Pharmaceutical Technology (Biotechnology), National Institute
  of Pharmaceutical Education and Research, Sector-67,,S. A. S.
  Nagar-160062, Punjab

author

Uttam C. Banerjee

• Department of
  Pharmaceutical Technology (Biotechnology), National Institute
  of Pharmaceutical Education and Research, Sector-67,,S. A. S.
  Nagar-160062, Punjab

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Identifiers

DOI

10.1515/boca-2015-0006