Copyright (c) 2023 Ravikanth Vysyaraju, V. Siddaiah, B. Hanumantha Rao, Subramanyeswara Rao, J. Venkateswarlu, K.V.V. Prasada Rao
This work is licensed under a Creative Commons Attribution 4.0 International License.
A Novel, Greener Synthesis and DFT Studies of Stereoisomers of Daclatasvir
Corresponding Author(s) : V. Siddaiah
Asian Journal of Chemistry,
Vol. 36 No. 1 (2024): Vol 36 Issue 1, 2024
Abstract
A novel and green method is reported to synthesize the stereoisomers of daclatasvir, an antiviral agent. This work mainly explains the
synthesis and characterization of two stereoisomers (S,S,R,S) and (R,S,R,R) of daclatasvir. The slow addition procedure was designed in order to get high yields in the presence of green solvents like DMSO, 2-methyl tetrahydrofuran and isopropyl alcohol. To gain a better understanding of the stability of intermediates, the DFT calculations were also carried out and presented.
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- L. Sandmann, B. Schulte, M.P. Manns and B. Maasoumy, Visc Med., 35, 161 (2019); https://doi.org/10.1159/000500963
- Y. Zhu and S. Chen, World J. Gastroenterol., 19, 8963 (2013); https://doi.org/10.3748/wjg.v19.i47.8963
- C. Hui, L. Biyue and K. Jingping, Method for Preparing Daclatasvir, Chinese Patent CN108069941 (2011).
- K. Jingping, L. Biyue, C. Sanping, C. Hui and W. Shuming, Method for Preparing Daclatasvir, Chinese Patent CN106188015 (2016).
- Y. Qing, X. Hai, C. Wenrul and B.S. Li, A Synthtic Method for Daclatasvir, Chinese Patent CN106256825 (2018).
- Q. Ye-feng, High Performance Liquid Chromatography Chiral Method for Separating Daclatasvir Dihydrochloride and Five Optical Isomers, Chinese Patent CN108680684A (2018).
- P. Anastas and N. Eghbali, Chem. Soc. Rev., 39, 301 (2010); https://doi.org/10.1039/B918763B
References
L. Sandmann, B. Schulte, M.P. Manns and B. Maasoumy, Visc Med., 35, 161 (2019); https://doi.org/10.1159/000500963
Y. Zhu and S. Chen, World J. Gastroenterol., 19, 8963 (2013); https://doi.org/10.3748/wjg.v19.i47.8963
C. Hui, L. Biyue and K. Jingping, Method for Preparing Daclatasvir, Chinese Patent CN108069941 (2011).
K. Jingping, L. Biyue, C. Sanping, C. Hui and W. Shuming, Method for Preparing Daclatasvir, Chinese Patent CN106188015 (2016).
Y. Qing, X. Hai, C. Wenrul and B.S. Li, A Synthtic Method for Daclatasvir, Chinese Patent CN106256825 (2018).
Q. Ye-feng, High Performance Liquid Chromatography Chiral Method for Separating Daclatasvir Dihydrochloride and Five Optical Isomers, Chinese Patent CN108680684A (2018).
P. Anastas and N. Eghbali, Chem. Soc. Rev., 39, 301 (2010); https://doi.org/10.1039/B918763B