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Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-ChloroMandelic Acid Ethyl Ester is used as a reactant for the chiral synthesis of α-hydroxy ketones, which are important intermediates in the development of pharmaceutical compounds. The chiral nature of this ester allows for the creation of enantiomerically pure products, which is crucial for the efficacy and safety of many drugs.
Used in Chemical Synthesis:
(S)-2-ChloroMandelic Acid Ethyl Ester is used as a versatile building block in the synthesis of various organic compounds. Its reactivity and selectivity make it a valuable component in the preparation of complex molecules and advanced materials.
Used in Research and Development:
(S)-2-ChloroMandelic Acid Ethyl Ester is utilized as a research tool in the study of asymmetric synthesis, enantioselective reactions, and the development of new synthetic methodologies. Its unique properties and reactivity contribute to the advancement of chemical science and the discovery of novel compounds with potential applications.

Upstream product

• 64-17-5 ethanol 
• 10421-85-9 2-chloromandelic acid 
• 66985-47-5 2-chloro-α-[(trimethylsilyl)oxy]benzeneacetonitrile 
• 40061-54-9 2-chlorophenylacetic acid ethyl ester 
• 62123-75-5 ethyl 2-(2-chlorophenyl)-2-oxoacetate 
• 13511-30-3 ethyl 2-(2-chlorophenyl)-2-hydroxyacetate 
• 1398179-33-3 o-chlorophenyldiazoacetic acid ethyl ester 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 421545-87-1 ethyl 2-(2-chlorophenyl)-2-hydroxyacetate 

Relevant academic research and scientific papers

Exploiting Cofactor Versatility to Convert a FAD-Dependent Baeyer–Villiger Monooxygenase into a Ketoreductase

Cyclohexanone monooxygenases (CHMOs) show very high catalytic specificity for natural Baeyer–Villiger (BV) reactions and promiscuous reduction reactions have not been reported to date. Wild-type CHMO from Acinetobacter sp. NCIMB 9871 was found to possess an innate, promiscuous ability to reduce an aromatic α-keto ester, but with poor yield and stereoselectivity. Structure-guided, site-directed mutagenesis drastically improved the catalytic carbonyl-reduction activity (yield up to 99 %) and stereoselectivity (ee up to 99 %), thereby converting this CHMO into a ketoreductase, which can reduce a range of differently substituted aromatic α-keto esters. The improved, promiscuous reduction activity of the mutant enzyme in comparison to the wild-type enzyme results from a decrease in the distance between the carbonyl moiety of the substrate and the hydrogen atom on N5 of the reduced flavin adenine dinucleotide (FAD) cofactor, as confirmed using docking and molecular dynamics simulations.

Boron-Catalyzed O-H Bond Insertion of α-Aryl α-Diazoesters in Water

A catalytic, metal-free O-H bond insertion of α-diazoesters in water in the presence of B(C6F5)3·nH2O (2 mol %) was developed, affording a series of α-hydroxyesters in good to excellent yields. The reaction features easy operation and wide substrate scope, and importantly, no metal is needed as compared with the conventional methods. Significantly, this approach further expands the applications of B(C6F5)3 under water-tolerant conditions.

A new class of tunable dendritic diphosphine ligands: Synthesis and applications in the Ru-catalyzed asymmetric hydrogenation of functionalized ketones

A series of tunable G0-G3 dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β-ketoesters, α-ketoesters, and α-ketoamides to reveal the effects of dendron size on the catalytic properties. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first-generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.

Stereospecific reduction of methyl o-chlorobenzoylformate at 300 g·L-1 without additional cofactor using a carbonyl reductase mined from Candida glabrata

In order to search for oxidoreductases suitable for the preparation of methyl (R)-o-chloromandelate [(R)-CMM], the key intermediate for clopidogrel, the homologous proteins of Gre2p were expressed in Escherichia coli, among which CgKR1 showed the most satisfactory activity and stereoselectivity towards methyl o-chlorobenzoylformate (CBFM). Using the crude enzyme of CgKR1 and glucose dehydrogenase (GDH), as much as 300 g·L-1 of CBFM was almost stoichiometrically converted to (R)-CMM with excellent enantiomeric excess (98.7% ee). More importantly, the reaction could be performed without external addition of an expensive cofactor. The substrate profile indicates that keto esters serve as the most suitable substrate, which was confirmed by gram-scale preparations. Homology modeling and docking analysis revealed the molecular basis for the high stereoselectivity of CgKR1. These demonstrate not only the feasibility of in silico mining of novel enzymes based on sequence homology but also the applicability of this new reductase for the practical production of optically active (R)-CMM. Copyright

Simply air: Vanadium-catalyzed oxidative kinetic resolution of methyl o-chloromandelate by ambient air

Vanadium-catalyzed oxidative kinetic resolution (OKR) of methyl o-chloromandelate 2a, key intermediate of the well-known oral antiplatelet agent (S)-clopidogrel, was achieved by ambient air for the first time. The air oxidation system, which was composed of vanadium and tridentate Schiff base ligands derived from amino alcohols and salicylaldehyde derivatives, afforded an efficient and economic approach to the target intermediate with high enantioselectivities (>99% ee).

A rapid and green approach to chiral α-hydroxy esters: asymmetric transfer hydrogenation (ATH) of α-keto esters in water by use of surfactants

A series of α-hydroxy esters were rapidly prepared (1.5 h) from α-keto esters via asymmetric transfer hydrogenation (ATH) in water by the use of surfactants for the first time. This green method, catalyzed by a water-soluble and recyclable Ru(II) complex, gave moderate to high enantioselectivities (up to 99.7% ee) with DTAB as an additive and HCOONa as the hydrogen source.

CeCl3·7H2O: An effective additive in ru-catalyzed enantioselective hydrogenation of aromatic α-ketoesters

(Chemical Equation Presented) In the presence of catalytic amounts of CeCl3·7H2O, [RuCl(benzene)(S)-SunPhos]Cl is a highly effective catalyst for the asymmetric hydrogenation of aromatic α-ketoesters. A variety of ethyl α-hydroxy-α-arylacetates have been prepared in up to 98.3% ee with a TON up to 10 000. Challenging aromatic α-ketoesters with ortho substituents are also hydrogenated with high enantioselectivities. The addition of CeCl3·7H2O not only improves the enantioselectivity but also enhances the stability of the catalyst. The ratio of CeCl3·7H2O to [RuCl(benzene)(S)-SunPhos]Cl plays an important role in the hydrogenation reaction with a large substrate/catalyst ratio.

Highly efficient chemoenzymatic synthesis of methyl (R)-o-chloromandelate, a key intermediate for clopidogrel, via asymmetric reduction with recombinant Escherichia coli

Methyl (R)-o-chloromandelate [(R)-1], which is an intermediate for a platelet aggregation inhibitor named clopidogrel, was obtained in >99% ee by the asymmetric reduction of methyl o-chlorobenzoylformate (2) with recombinant Escherichia coli overproducing

THE METHOD OF MAKING OPTICALLY ACTIVE 2-CHLOROMANDELIC ACID ESTERS AND 2-CHLOROMANDELIC ACIDS BY ENZYMATIC METHOD

The present invention relates to process for the preparation of optically active 2-chloromandelic acid esters represented by the general formula 2 and optically active 2-chloromandelic acids represented by the general formula 2 which are used intensively as important chiral intermediates. In more detail, this invention relates to the process for preparing optically active 2-chloromandelic acid esters and optically active 2-chloromandelic acids by stereospecific hydrolysis of racemic 2-chloromandelic acid ester using lipases or lipase-producing microorganisms in the aqeous phase or organic phase including aqeous solvent. The method of making optically active 2-chloromandelic aicd esters and their acids is usful in the practical process because production of seperation of compounds with high optical purity are easy.

Highly enantioselective and efficient synthesis of methyl (R)-o-chloromandelate with recombinant E. coli: Toward practical and green access to clopidogrel

Methyl (R)-o-chloromandelate ((R)-1), which is an intermediate for a platelet aggregation inhibitor named clopidogrel, was obtained in >99% ee by the asymmetric reduction of methyl o-chlorobenzoylformate (2) (up to 1.0 M) with recombinant E. coli overprod