Stereoselective Amination of Chiral Benzylic Ethers Using Chlorosulfonyl Isocyanate: Total Synthesis of (+)-Sertraline

Lee, Sang Hwi; Kim, In Su; Li, Qing Ri; Guang, Dong; Jeong, Lak Shin; Jung, Young Hoon

doi:10.1021/jo201794k

Cited by 50 publications

(14 citation statements)

References 57 publications

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“…> 99%. 55 87 Therefore, it is possible to affirm that the biocatalyst produced in this article (CALB-IB-350 and CALB-GLX) was more efficient in the kinetic resolution of rac-indanyl acetate than the commercial enzyme (Novozyme435). Other specifications are described in methods.…”

Section: Application Of the Biocatalyst In Resolution Of Racemic Mixtmentioning

confidence: 64%

“…= 97%, while the value reported in the literature was [ α ] D = −30.6 (c 1.0; CHCl 3 ) e.e. > 99% . For the ( S )‐indanyl acetate was obtained [ α ] D = −86,8 (c 1.0; CHCl 3 ) e.e.…”

Section: Resultsmentioning

confidence: 99%

“…These drugs were used in the treatment of depression, a nonselective monoamine transporter inhibitor, for the treatment of Parkinson's disease, to treat HIV infections and antihypertensive effects, respectively. 55 Preliminary results in our laboratory indicated that commercial Novozyme 435 (interfacially immobilized CALB on a hydrophobic Lewatic resin) 56 was quite inefficient in the resolution of this product. The objective of this article was to optimize the immobilization of CALB on IB-350 via multipoint covalent attachment and to compare the performance of the new biocatalyst with Novozyme 435 and gyoxyl-agarose-CALB.…”

Section: Introductionmentioning

confidence: 98%

“…Other substances used as intermediates in the synthesis of enantiomerically pure drugs is the ( R )‐indanol and ( S )‐indanyl acetate, which are precursors in the synthesis of the (+)‐Sertraline (Zoloft®), (+)‐Indatraline, Rasagiline (Azilect®), Indinavir (Crixivan®), and Irindalone. These drugs were used in the treatment of depression, a nonselective monoamine transporter inhibitor, for the treatment of Parkinson's disease, to treat HIV infections and antihypertensive effects, respectively . Preliminary results in our laboratory indicated that commercial Novozyme 435 (interfacially immobilized CALB on a hydrophobic Lewatic resin) was quite inefficient in the resolution of this product.…”

Section: Introductionmentioning

confidence: 99%

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Kinetic resolution of drug intermediates catalyzed by lipase B from Candida antarctica immobilized on immobead‐350

Pinheiro

Rios

Fonseca

et al. 2018

Biotechnology Progress

108

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Novozyme 435, which is a commercial immobilized lipase B from Candida antarctica (CALB), has been proven to be inadequate for the kinetic resolution of rac-indanyl acetate. As it has been previously described that different immobilization protocols may greatly alter lipase features, in this work, CALB was covalently immobilized on epoxy Immobead-350 (IB-350) and on glyoxyl-agarose to ascertain if better kinetic resolution would result. Afterwards, all CALB biocatalysts were utilized in the hydrolytic resolution of rac-indanyl acetate and rac-(chloromethyl)-2-(o-methoxyphenoxy) ethyl acetate. After optimization of the immobilization protocol on IB-350, its loading capacity was 150 mg protein/g dried support. Furthermore, the CALB-IB-350 thermal and solvent stabilities were higher than that of the soluble enzyme (e.g., by a 14-fold factor at pH 5-70°C and by a 11-fold factor in dioxane 30%-65°C) and that of the glyoxyl-agarose-CALB (e.g., by a 12-fold factor at pH 10-50°C and by a 21-fold factor in dioxane 30%-65°C). The CALB-IB-350 preparation (with 98% immobilization yield and activity versus p-nitrophenyl butyrate of 6.26 ± 0.2 U/g) was used in the hydrolysis of rac-indanyl acetate using a biocatalyst/substrate ratio of 2:1 and a pH value of 7.0 at 30°C for 24 h. The conversion obtained was 48% and the enantiomeric excess of the product (e.e. ) was 97%. These values were much higher than the ones obtained with Novozyme 435, 13% and 26% of conversion and e.e.p, respectively. © 2018 American Institute of Chemical Engineers Biotechnol. Prog., 34:878-889, 2018.

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Section: Application Of the Biocatalyst In Resolution Of Racemic Mixtmentioning

confidence: 64%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Kinetic resolution of drug intermediates catalyzed by lipase B from Candida antarctica immobilized on immobead‐350

Pinheiro

Rios

Fonseca

et al. 2018

Biotechnology Progress

108

View full text Add to dashboard Cite

show abstract

“…asc.wiley-vch.de condensation of 1-napthol and 1,2-dichlorobenzene in the presence of a strong Lewis acid. [24] Enantiopure (4S)-tetralone 22 was also reduced and acetylated. The tetralin core (α-or β-substituted) is in itself a privileged moiety in drug discovery, being present in a number of drugs and bioactive compounds.…”

Section: Full Papermentioning

confidence: 97%

Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst

et al. 2019

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Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents (i. e. isopropyl or tert-butyl groups) on the β-carbon, which is in contrast to previously tested commercially available enzymes which displayed a preference for substrates with sterically less demanding substituents (e.g. methyl group) at the β-carbon.

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Enabling Modular Click Chemistry Library through Sequential Ligations of Carboxylic Acids and Amines

Wang,

Zhou,

et al. 2024

Angewandte Chemie

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High‐throughput synthesis and screening of chemical libraries play pivotal roles in drug discovery. Click chemistry has emerged as a powerful strategy for constructing highly modular chemical libraries. However, the development of new click reactions and unlocking new click able building blocks remain exceedingly challenging. Here in , we describe a double‐click strategy that enables the sequential ligation of widely available carboxylic acids and amines with fluorosulfuryl isocyanate (FSO 2 NCO) via a modular amidation/SuFEx process. This method provides facile access to chemical libraries of N‐fluorosulfonyl amides (RCONHSO 2 F) and N‐acylsulfamides (RCONHSO 2 NR ´ R ´´ ) in near‐quantitative yields under simple and practical conditions. The robustness and efficiency of this double click strategy is showcased by the facile construction of chemical libraries in 96‐well microtiter plates from a large number of carboxylic acids and amines. Preliminary biological activity screening reveals that some compound s exhibit high antimicrobial activities against Gram‐positive bacterium S. aureus and drug‐resistant MRSA (MIC up to 6.25·μg mL‐1). These results provide compelling evidence for the potential application of modular click chemistry library as an enabling technology in high‐throughput medicinal chemistry.

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Stereoselective Amination of Chiral Benzylic Ethers Using Chlorosulfonyl Isocyanate: Total Synthesis of (+)-Sertraline

Abstract: The stereoselective amination of various chiral benzylic ethers using chlorosulfonyl isocyanate is developed, and the application of this method to the total synthesis of a potent antidepressant, (+)-sertraline, from readily available 1-naphthol is also described.

Cited by 50 publications

References 57 publications

Kinetic resolution of drug intermediates catalyzed by lipase B from Candida antarctica immobilized on immobead‐350

Kinetic resolution of drug intermediates catalyzed by lipase B from Candida antarctica immobilized on immobead‐350

Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst

Enabling Modular Click Chemistry Library through Sequential Ligations of Carboxylic Acids and Amines

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