Studies on the dynamic resolution of Crizotinib intermediate

被引：7
作者：
de Franca, Alexandre da S. [1 ]
Silva, Marcus V. M. [1 ]
Neves, Rebeca V. [1 ]
de Souza, Stefania P. [1 ]
Leao, Raquel A. C. [1 ,2 ]
Monteiro, Carlos M. [3 ]
Rocha, Angelo [4 ]
Afonso, Carlos A. M. [3 ]
de Souza, Rodrigo O. M. A. [1 ,2 ]
机构：
[1] Univ Fed Rio de Janeiro, Chem Inst, Biocatalysis & Organ Synth Grp, Rio De Janeiro, Brazil
[2] Univ Fed Rio de Janeiro, Pharm Sch, Rio De Janeiro, Brazil
[3] Univ Lisbon, Fac Pharm, Res Inst Med iMed ULisboa, Av Prof Gama Pinto, P-1649003 Lisbon, Portugal
[4] Univ Lisbon, Inst Super Tecn, Inst Bioengn & Biosci, Dept Bioengn, Lisbon, Portugal
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2018年 / 26卷 / 07期
关键词：
Kinetic resolution; Lipases; Dynamic resolution; Crizotinib; Continuous-flow; KINETIC RESOLUTION; SECONDARY ALCOHOLS; MESOPOROUS-SILICA; COMBO CATALYSIS; FLOW SYNTHESIS; RACEMIZATION; CANCER; RUTHENIUM; OXIDATION; LIPASES;
D O I：
10.1016/j.bmc.2017.07.024
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Crizotinib is an anti-cancer agent approved for treatment of non-small cell lung carcinoma. Retrosynthetic analysis revels 1-(2,6-dichloro-3-fluorophenyl) ethanol as an important intermediate, which can be made available by different biocatalytic approaches. Herein we report our results on the kinetic and dynamic resolution towards the desired chiral intermediate for Crizotinib synthesis. The results obtained show that very good conversions and high selectivity could be obtained for the kinetic resolution (45% conv. and E > 200) while dynamic kinetic resolution under continuous-flow conditions afforded the desired product in 57% conversion and 98% e.e. (C) 2017 Published by Elsevier Ltd.
引用
收藏
页码：1333 / 1337
页数：5
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