Studies on the dynamic resolution of Crizotinib intermediate

França, Alexandre da S.; Silva, Marcus V. M.; Neves, Rebeca V.; Souza, Stefânia P. de; Leão, Raquel A. C.; Monteiro, Carlos M.; Rocha, Álvaro; Afonso, Carlos A. M.; Souza, Rodrigo O. M. A. de

doi:10.1016/j.bmc.2017.07.024

Cited by 12 publications

(5 citation statements)

References 30 publications

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“…After 5 days with a flow rate of 0.5 mL/min, 57% conversion of the acetylated (R)isomer (96% ee) was attained. 59 2.1.5. DKR of Amines.…”

Section: Flow Chemistrymentioning

confidence: 99%

“…The same group developed the DKR of 1-(2,6-dichloro-3-fluorophenyl)ethanol (100 mM), an intermediate for the synthesis of the anticancer agent Crizotinib, under flow conditions applying different layers of immobilized CAL-B (Novozym 435) and VOSO 4 · x H 2 O in the presence of isopropenyl acetate (100 mM) as an acylating agent in iso -octane at 80 °C. After 5 days with a flow rate of 0.5 mL/min, 57% conversion of the acetylated ( R )-isomer (96% ee ) was attained …”

Section: Metal–enzyme Cascades Using Individual Catalystsmentioning

confidence: 99%

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Expanding the Synthetic Toolbox through Metal–Enzyme Cascade Reactions

et al. 2023

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The combination of metal-, photo-, enzyme-, and/or organocatalysis provides multiple synthetic solutions, especially when the creation of chiral centers is involved. Historically, enzymes and transition metal species have been exploited simultaneously through dynamic kinetic resolutions of racemates. However, more recently, linear cascades have appeared as elegant solutions for the preparation of valuable organic molecules combining multiple bioprocesses and metal-catalyzed transformations. Many advantages are derived from this symbiosis, although there are still bottlenecks to be addressed including the successful coexistence of both catalyst types, the need for compatible reaction media and mild conditions, or the minimization of cross-reactivities. Therefore, solutions are here also provided by means of catalyst coimmobilization, compartmentalization strategies, flow chemistry, etc. A comprehensive review is presented focusing on the period 2015 to early 2022, which has been divided into two main sections that comprise first the use of metals and enzymes as independent catalysts but working in an orchestral or sequential manner, and later their application as bionanohybrid materials through their coimmobilization in adequate supports. Each part has been classified into different subheadings, the first part based on the reaction catalyzed by the metal catalyst, while the development of nonasymmetric or stereoselective processes was considered for the bionanohybrid section.

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“…After 5 days with a flow rate of 0.5 mL/min, 57% conversion of the acetylated (R)isomer (96% ee) was attained. 59 2.1.5. DKR of Amines.…”

Section: Flow Chemistrymentioning

confidence: 99%

Section: Metal–enzyme Cascades Using Individual Catalystsmentioning

confidence: 99%

Expanding the Synthetic Toolbox through Metal–Enzyme Cascade Reactions

et al. 2023

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“…Lima et al [25] used two different lipases, differing in selectivity, for the synthesis of Pindolol, a nonselective β-blocker. Firstly, lipase from Lipase from Candida antarctica B Crizotinib [22] Immobilized lipase from Candida antarctica B Buprenorphine [23] Lipase from Thermomyces lanuginosus and immobilized lipase from Candida antarctica B Methotrexate [24] Lipases from Pseudomonas fluorescens and Candida rugosa Pindolol [25] Lipase from Candida rugosa Propranolol [26] Lipase from Aspergillus oryzae (WZ007) Brivaracetam [27] Lipase from Candida antarctica B Practolol, Pindolol, and Carteolol [28] Pseudomonas fluorescens was applied on the kinetic resolution of one drug intermediate, followed by the hydrolysis of the other intermediate by a lipase from Candida rugosa. The final drug was isolated in quantitative yield with an excellent enantiomeric excess (ee 97%).…”

Section: Pharmaceutical Applicationsmentioning

confidence: 99%

Chemical modification of lipases: A powerful tool for activity improvement

Noro

Cavaco‐Paulo

Silva

2022

Biotechnology Journal

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The demand for adequate and ecologically acceptable procedures to produce the most differentiated products has been growing in recent decades, with enzymes being excellent examples of the advances achieved so far. Lipases are astonishing catalysts with a vast range of applications including the synthesis of esters, flavors, biodiesel, and polymers. The broad specificity of the substrates, as well as the regio-, stereo-, and enantioselectivity, are the differentiating factors of these enzymes. Structural modification is a current approach to enhance the activity of lipases. Chemical modification of lipases to improve catalytic performance is of great interest considering the increasingly broad fields of application. Together with the physical immobilization onto solid supports, different strategies have been developed to produce catalysts with higher activity and stability. In this review, practical insights into the different strategies developed in recent years regarding the modification of lipases are described. For the first time, the impact of the modifications on the activity and stability of lipases, as well as on the biotechnological applications, is fully compiled.

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“…A chiral benzyl alcohol, namely the (R)-1-(2,6-dichloro-3-fluorophenyl)ethanol is the key-intermediate in the synthesis of Crizotinib (Scheme 12). The continuous flow-DKR of the racemate using Novozym ® 435 and VOSO 4 •XH 2 O allowed to circumvent the incompatibility between bio-and chemo-catalyst: better conversion was obtained in comparison to batch reaction [50]. A heterogeneous catalyst based on size-controlled (2.8 nm) palladium nanoparticles highly dispersed on mesoporous silica, as a support (Pd@SBA-15) was synthesized in 2017 by Li and coworkers [51].…”

Section: Scheme 11 Continuous-flow Dkr Of An Allylic Alcoholmentioning

confidence: 99%

Progress on the Stereoselective Synthesis of Chiral Molecules Based on Metal-Catalyzed Dynamic Kinetic Resolution of Alcohols with Lipases

Ferraccioli¹

2021

Symmetry

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Metal/lipase-combo catalyzed dynamic kinetic resolution (DKR) of racemic chiral alcohols is a general and practical process to obtain the corresponding enantiopure esters R with quantitative conversion. The use of known Ru-catalysts as well as newly developed homogeneous and heterogeneous metal catalysts (Fe, V) contributed to make the DKR process more sustainable and to expand the substrate scope of the reaction. In addition to classical substrates, challenging allylic alcohols, tertiary alcohols, C1-and C2-symmetric biaryl diols turned out to be competent substrates. Synthetic utility further emerged from the integration of this methodology into cascade reactions leading to linear/cyclic chiral molecules with high ee through the formation of multiple bonds, in a one-pot procedure.

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Studies on the dynamic resolution of Crizotinib intermediate

Cited by 12 publications

References 30 publications

Expanding the Synthetic Toolbox through Metal–Enzyme Cascade Reactions

Expanding the Synthetic Toolbox through Metal–Enzyme Cascade Reactions

Chemical modification of lipases: A powerful tool for activity improvement

Progress on the Stereoselective Synthesis of Chiral Molecules Based on Metal-Catalyzed Dynamic Kinetic Resolution of Alcohols with Lipases

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