7292-70-8

Usage

Uses

Used in Pharmaceutical Industry:
DL-2-(4-CHLOROPHENYL)GLYCINE is used as a building block for the synthesis of various pharmaceuticals due to its ability to inhibit the glycine receptor, which is a potential therapeutic target for neurological disorders.
Used in Agrochemical Industry:
DL-2-(4-CHLOROPHENYL)GLYCINE is used as a building block in the synthesis of agrochemicals, contributing to the development of new compounds for agricultural applications.
Used in Asymmetric Catalysis:
DL-2-(4-CHLOROPHENYL)GLYCINE is used as a chiral auxiliary in asymmetric catalysis, playing a crucial role in the synthesis of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical processes.
Used in Synthesis of Bioactive Compounds:
DL-2-(4-CHLOROPHENYL)GLYCINE is used as a starting material for the synthesis of other bioactive compounds, expanding its applications in the field of medicinal chemistry and drug discovery.

Upstream product

• 6212-32-4 5-(p-chlorophenyl)hydantoin 
• 104-88-1 4-chlorobenzaldehyde 
• 7477-64-7 1-(p-chlorophenyl)-1,2-ethanediol 
• 1073-67-2 4-vinylbenzyl chloride 
• 56464-72-3 2-amino-2-(p-chlorophenyl)acetonitrile 
• 43189-43-1 (R)-Amino-(4-chloro-phenyl)-acetic acid methylester 
• 7138-34-3 p-chloromandelic acid 
• 92303-74-7 4-chloro-(RS)-phenylglycinamide hydrochloride 
• 102333-75-5 2-amino-2-(4-chlorophenyl)acetamide 
• 856214-68-1 4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)benzylideneamine 
• 112022-98-7 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-{[(R)-tert-butylcarbamoyl-(4-chloro-phenyl)-methyl]-formyl-amino}-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 144744-27-4 (3R,5S,6R)-2,3,5,6-Tetrahydro-3-(p-chlorophenyl)-5,6-diphenyl-1,4-oxazin-2-one 
• 119825-44-4 (R)-2-Amino-N-tert-butyl-2-(4-chloro-phenyl)-acetamide; hydrochloride 
• 67-66-3 chloroform 

Downstream Products

• 43189-43-1 (R)-Amino-(4-chloro-phenyl)-acetic acid methylester 
• 110315-00-9 2-(4-chlorophenyl)-N-(4-methylbenzoyl)glycine 
• 43189-37-3 (R)-2-amino-2-(4-chlorophenyl)acetic acid 
• 122454-22-2 C₁₀H₅ClF₃NO₂ 

Relevant academic research and scientific papers

Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine

The transamination of α-keto acids with 2-phenylglycine is an effective methodology for directly synthesizing unprotected α-amino acids. However, the synthesis of 2-arylglycines by transamination is problematic because the corresponding products, 2-arylglycines, transaminate the starting arylglyoxylic acids. Herein, we demonstrate the use of commercially available l-2-(2-chlorophenyl)glycine as the nitrogen source in the transamination of arylglyoxylic acids, producing the corresponding 2-arylglycines without interference from the undesired self-transamination process.

Method for continuously and quickly preparing DL-phenylglycine and analogue thereof

The invention provides a method for continuously and quickly preparing DL-phenylglycine and an analogue thereof. The method comprises the steps of adding 2-hydroxyl-phenylacetonitrile and an analoguethereof (cyanohydrin for short) and an aqueous ammonium bicarbonate solution into a microchannel reactor for a reaction, controlling the reaction temperature to be 80-130 DEG C, and controlling the reaction pressure to be 0.5-2.0 MPa, wherein the standing time of the reactants in a microchannel is 1-8 min, and an aqueous solution of 5-phenyl-hydantoin and an analogue thereof (hydantoin for short)is obtained; adding the hydantoin and alkali into the microchannel reactor for a reaction, controlling the reaction temperature to be 120-200 DEG C, and controlling the reaction pressure to be 1.0-3.5MPa, wherein the standing time of the reactants in the microchannel is 1-8 min, and then a saline solution of phenylglycine and an analogue thereof is obtained; conducting acidification neutralization and crystallization to obtain the phenylglycine and the analogue thereof. According to the method, the microchannel reactor is adopted, the reaction time is greatly shorted, the reaction speed is increased, pyrolysis and polymerization of the cyanohydrin are reduced, no by-products are generated, the products are high in yield, clean and environmentally friendly, and the production cost is lowered.

One-Pot Enantioselective Synthesis of d-Phenylglycines from Racemic Mandelic Acids, Styrenes, or Biobased l-Phenylalanine via Cascade Biocatalysis

Enantiopure d-phenylglycine and its derivatives are an important group of chiral amino acids with broad applications in thepharmaceutical industry. However, the existing synthetic methods for d-phenylglycine mainly rely on toxic cyanide chemistry and multistep processes. To provide green and safe alternatives, we envisaged cascade biocatalysis for the one-pot synthesis of d-phenylglycine from racemic mandelic acid, styrene, and biobased l-phenylalanine, respectively. Recombinant Escherichia coli (LZ110) was engineered to coexpress four enzymes to catalyze a 3-step reaction in one pot, transforming mandelic acid (210 mM) to give enantiopure d-phenylglycine in 29.5 g L?1 (195 mM) with 93% conversion. Using the same whole-cell catalyst, twelve other d-phenylglycine derivatives were also produced from the corresponding mandelic acid derivatives in high conversion (58–94%) and very high ee (93–99%). E. coli (LZ116) expressing seven enzymes was constructed for the transformation of styrene to enantiopure d-phenylglycine in 80% conversion via a one-pot 6-step cascade biotransformation. Twelve substituted d-phenylglycines were also produced from the corresponding styrene derivatives in high conversion (45–90%) and very high ee (92–99%) via the same cascade reactions. A nine-enzymeexpressing E. coli (LZ143) was engineered to transform biobased l-phenylalanine to enantiopure d-phenylglycine in 83% conversion via a one-pot 8-step transformation. Preparative biotransformations were also demonstrated. The high-yielding synthetic methods use cheap and green reagents (ammonia, glucose, and/or oxygen), and E. coli whole-cell catalysts, thus providing green and useful alternative methods for manufacturing d-phenylglycine. (Figure presented.).

Preparation method for D, L-phenylglycine and analogue thereof

The invention provides a preparation method for D, L-phenylglycine and an analogue thereof. According to the method, benzaldehyde, an analogue thereof and hydrocyanic acid are adopted as raw materials and subjected to cyanidation reaction, and then 2-hydroxy-benzyl cyanide or 2-hydroxy-benzyl cyanide analogue (cyanohydrin for short) is generated. Cyanohydrin reacts with carbon dioxide and the aqueous solution of ammonia, and then 5-phenyl-hydantoin and an analogue thereof (hydantoin for short) are generated. hydantoin is successively subjected to steam stripping, alkaline hydrolysis, steam stripping, decolorization, neutralization, crystallization, washing, centrifuging, drying and the like to obtain D, L-phenylglycine and the analogue thereof. Compared with the prior art, the preparation method for D, L-phenylglycine and the analogue thereof can significantly and effectively reduce the pollution, and fewer inorganic salt by-products are generated. Meanwhile, the prepared D, L-phenylglycine and the analogue thereof are high in product yield and high in purity. Counted in benzaldehyde and the analogue thereof, the yield of D, L-phenylglycine and the analogue thereof is larger than or equal to 96%, and the product purity is larger than or equal to 99%. Meanwhile, the process flow is simple and feasible, so that the method is worthy of market popularization and application.

Ru-catalyzed C[sbnd]H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates

The reaction of N-unprotected methylesters of phenylglycine derivatives (1a–1f) with electron-rich internal alkynes (2a–2e), catalyzed by [Ru(cymene)Cl2]2 (10%), gives the corresponding 3,4-disubstituted isoquinoline-1-carboxylates 3 through C[sbnd]H/N[sbnd]H oxidative coupling. The C[sbnd]H bond activation step is assisted by carboxylates, and N-fluoro-2,4,6-trimethylpyridinium triflate works as the terminal oxidant. The process shows a remarkable tolerance to the presence of diverse electron-releasing and electron-attracting functional groups at the phenyl ring of the amino acid. In addition, the reaction of phenylglycine derivatives (1a–1f) with methyl acrylate (4a) catalyzed by [Ru(cymene)Cl2]2 (10%) under the same experimental conditions, gives the corresponding 3,N-disubstituted isoindoline-1-carboxylates 5 through C[sbnd]H/N[sbnd]H coupling. Isoindolines 5 are obtained as a mixture of diastereoisomers, with moderate to high values of diastereomeric excess (up to 80%).

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

High yield synthesis of d-phenylglycine and its derivatives by nitrilase mediated dynamic kinetic resolution in aqueous-1-octanol biphasic system

A strategy of nitrilase mediated dynamic kinetic resolution toward the synthesis of d-phenylglycine was developed, using aqueous-1-octanol biphasic system. Due to the efficient suppression of the decomposition of phenylglycinonitrile, a maximum yield of 81% is obtained. This result indicates that the nitrilase mediated dynamic kinetic resolution is a promising method toward the synthesis of d-phenylglycine and its derivatives.

Primary amines by transfer hydrogenative reductive amination of ketones by using cyclometalated IrIII catalysts

Cyclometalated iridium complexes are found to be versatile catalysts for the direct reductive amination (DRA) of carbonyls to give primary amines under transfer-hydrogenation conditions with ammonium formate as both the nitrogen and hydrogen source. These complexes are easy to synthesise and their ligands can be easily tuned. The activity and chemoselectivity of the catalyst towards primary amines is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Both aromatic and aliphatic primary amines were obtained in high yields. Moreover, a first example of homogeneously catalysed transfer-hydrogenative DRA has been realised for β-keto ethers, leading to the corresponding β-amino ethers. In addition, non-natural α-amino acids could also be obtained in excellent yields with this method. Reduce the work! A broad range of ketones have been successfully aminated to afford primary amines under transfer-hydrogenation conditions by using ammonium formate as the amine source and 0.1 mol % of a cyclometalated IrIII catalyst (see scheme). Copyright

Synthesis, insecticidal and acaricidal activities of novel 2-arylpyrroles

To search for novel 2-arylpyrroles with unique biological activities, a series of novel 2-arylpyrrole derivatives were designed and synthesized, and their structures were characterized by 1H and 13C NMR spectroscopy, MS spectrometry, and elemental analysis. Their insecticidal activities against Lepidopteran pests (e.g. Mythimna separata) and acaricidal activities against mites (e.g. Tetranychus urticae) were evaluated. The results of bioassays indicate that some of these title compounds exhibited excellent insecticidal and acaricidal activities. For example, 4-bromo-1-((chloromethoxy) methyl)-2-(4-chloro phenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (6a), 4-bromo-2-(4-chlorophenyl)-1-((2-fluoroethoxy)-methyl)-5-(trifluoromethyl) pyrrole-3-carbonitrile (6d) showed insecticidal activity against Mythimna separata and 4-bromo-2-(4-chlorophenyl)-1-((isopropoxymethoxy)methyl)-5- (trifluoro methyl)pyrrole-3-carbonitrile (7d) showed acaricidal activity against Tetranychus urticae. They were more effective than Chlorfenapyr, which has been the only commercialized member of a new class of chemicals of 2-arylpyrroles.

CATALYST COMPOUNDS

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.