Lipase mediated new chemo‐enzymatic synthesis of (RS)‐, (R)‐, and (S)‐bunolol

Author:

Patlolla Ravinder Reddy12,Deepthi Pulivarthi3,Raveena Gajjala12,Rosangzuala Khawlhring12,Tejaswini Somarowthu1,Prakasham Reddy Shetty1,Banoth Linga12ORCID

Affiliation:

1. Organic Synthesis and Process Chemistry Division CSIR‐Indian Institute of Chemical Technology Hyderabad India

2. Academy of Scientific and Innovative Research (AcSIR) Ghaziabad India

3. Fluoro Agrochemicals CSIR‐Indian Institute of Chemical Technology Hyderabad India

Abstract

AbstractThe β‐adrenergic receptor blocking agents are an important class of drug molecules. The present study reports a new chemo and chemo‐enzymatic synthetic process for (RS)‐, (R)‐, and (S)‐bunolol, one of the potent β‐adrenergic receptor blocker. In chemo‐enzymatic process, CAL L4777 lipase was employed for enantioselective kinetic resolution to synthesize the enantiopure (R)‐alcohol and (S)‐ester from the corresponding racemic alcohol. Thereafter, the corresponding (R)‐alcohol and deacylated (S)‐ester were treated with tert‐butylamine to produce (S)‐ and (R)‐bunolol, respectively. In chemical approach, epichlorohydrin (RS‐, R‐, and S‐) was used as a starting material via respective (RS)‐, (S)‐, and (R)‐glycidyl ether as intermediates for synthesis of enantiomeric (RS)‐, (R)‐, and (S)‐bunolol. In comparison between two approaches, it was found that the chemo‐enzymatic process was more effective and resulted in enantiomeric excess of 98% with 35% yield.

Publisher

Wiley

Subject

Organic Chemistry,Spectroscopy,Drug Discovery,Pharmacology,Catalysis,Analytical Chemistry

Reference49 articles.

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