Design and Enantiopure Synthesis of(R)-2-((2-Oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: A Key Precursor to Build 2-Oxazolidinone Class of Antibacterial Agents

Design and Enantiopure Synthesis of(R)-2-((2-Oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: A Key Precursor to Build 2-Oxazolidinone Class of Antibacterial Agents

A new synthetic method for the preparation of high enantiopure (R)-2-((2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione has been developed. The enantiopurity of the obtained (R)-2-((2-oxooxazolidin-5-yl)methyl) isoindoline-1,3-dione is established using chiral high performance liquid chromatogr...

Full description

Bibliographic Details
Main Authors: T. Rajesh, P. Suryanarayana Reddy, M. Manidhar, M. Vijaya Lakshmi, G. Madhusudhan
Format: Article
Language:English
Published: Hindawi Limited 2011-01-01
Series:E-Journal of Chemistry
Online Access:http://dx.doi.org/10.1155/2011/893270
id doaj-595c2ade9ed84d05b29b1d6c9acb8a92
record_format Article
spelling doaj-595c2ade9ed84d05b29b1d6c9acb8a922020-11-24T22:09:15ZengHindawi LimitedE-Journal of Chemistry0973-49452090-98102011-01-01831417142310.1155/2011/893270Design and Enantiopure Synthesis of(R)-2-((2-Oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: A Key Precursor to Build 2-Oxazolidinone Class of Antibacterial AgentsT. Rajesh0P. Suryanarayana Reddy1M. Manidhar2M. Vijaya Lakshmi3G. Madhusudhan4Department of Research and Development, Inogent Laboratories Private Limited (A GVK BIO Company), 28A, IDA, Nacharam, Hyderabad-500 076, IndiaDepartment of Research and Development, Inogent Laboratories Private Limited (A GVK BIO Company), 28A, IDA, Nacharam, Hyderabad-500 076, IndiaDepartment of Research and Development, Inogent Laboratories Private Limited (A GVK BIO Company), 28A, IDA, Nacharam, Hyderabad-500 076, IndiaDepartment of Aanlytical Research and Development, Inogent Laboratories Private Limited, 28A, IDA, Nacharam, Hyderabad-500 076, IndiaDepartment of Research and Development, Inogent Laboratories Private Limited (A GVK BIO Company), 28A, IDA, Nacharam, Hyderabad-500 076, IndiaA new synthetic method for the preparation of high enantiopure (R)-2-((2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione has been developed. The enantiopurity of the obtained (R)-2-((2-oxooxazolidin-5-yl)methyl) isoindoline-1,3-dione is established using chiral high performance liquid chromatography (HPLC) i.e. enantiomeric excess (ee) as 100%. One among the two proposed approaches, is succeeded in preparing enantiopure targeted chiral building block using (R)-2-(chloromethyl)oxirane ((R)-epichlorohydrin) as precursor. This heterocyclic 2-oxazolidinone moiety could be useful to prepare a series of antibacterial agents containing 2-oxazolidinone.http://dx.doi.org/10.1155/2011/893270
collection DOAJ
language English
format Article
sources DOAJ
author T. Rajesh
P. Suryanarayana Reddy
M. Manidhar
M. Vijaya Lakshmi
G. Madhusudhan
spellingShingle T. Rajesh
P. Suryanarayana Reddy
M. Manidhar
M. Vijaya Lakshmi
G. Madhusudhan
Design and Enantiopure Synthesis of(R)-2-((2-Oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: A Key Precursor to Build 2-Oxazolidinone Class of Antibacterial Agents
E-Journal of Chemistry
author_facet T. Rajesh
P. Suryanarayana Reddy
M. Manidhar
M. Vijaya Lakshmi
G. Madhusudhan
author_sort T. Rajesh
title Design and Enantiopure Synthesis of(R)-2-((2-Oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: A Key Precursor to Build 2-Oxazolidinone Class of Antibacterial Agents
title_short Design and Enantiopure Synthesis of(R)-2-((2-Oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: A Key Precursor to Build 2-Oxazolidinone Class of Antibacterial Agents
title_full Design and Enantiopure Synthesis of(R)-2-((2-Oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: A Key Precursor to Build 2-Oxazolidinone Class of Antibacterial Agents
title_fullStr Design and Enantiopure Synthesis of(R)-2-((2-Oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: A Key Precursor to Build 2-Oxazolidinone Class of Antibacterial Agents
title_full_unstemmed Design and Enantiopure Synthesis of(R)-2-((2-Oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: A Key Precursor to Build 2-Oxazolidinone Class of Antibacterial Agents
title_sort design and enantiopure synthesis of(r)-2-((2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione: a key precursor to build 2-oxazolidinone class of antibacterial agents
publisher Hindawi Limited
series E-Journal of Chemistry
issn 0973-4945
2090-9810
publishDate 2011-01-01
description A new synthetic method for the preparation of high enantiopure (R)-2-((2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione has been developed. The enantiopurity of the obtained (R)-2-((2-oxooxazolidin-5-yl)methyl) isoindoline-1,3-dione is established using chiral high performance liquid chromatography (HPLC) i.e. enantiomeric excess (ee) as 100%. One among the two proposed approaches, is succeeded in preparing enantiopure targeted chiral building block using (R)-2-(chloromethyl)oxirane ((R)-epichlorohydrin) as precursor. This heterocyclic 2-oxazolidinone moiety could be useful to prepare a series of antibacterial agents containing 2-oxazolidinone.
url http://dx.doi.org/10.1155/2011/893270
work_keys_str_mv AT trajesh designandenantiopuresynthesisofr22oxooxazolidin5ylmethylisoindoline13dioneakeyprecursortobuild2oxazolidinoneclassofantibacterialagents
AT psuryanarayanareddy designandenantiopuresynthesisofr22oxooxazolidin5ylmethylisoindoline13dioneakeyprecursortobuild2oxazolidinoneclassofantibacterialagents
AT mmanidhar designandenantiopuresynthesisofr22oxooxazolidin5ylmethylisoindoline13dioneakeyprecursortobuild2oxazolidinoneclassofantibacterialagents
AT mvijayalakshmi designandenantiopuresynthesisofr22oxooxazolidin5ylmethylisoindoline13dioneakeyprecursortobuild2oxazolidinoneclassofantibacterialagents
AT gmadhusudhan designandenantiopuresynthesisofr22oxooxazolidin5ylmethylisoindoline13dioneakeyprecursortobuild2oxazolidinoneclassofantibacterialagents
_version_ 1725812817208016896

Similar Items