20334-70-7

Usage

Uses

Used in Pharmaceutical Synthesis:
(2R)-2-chloro-3-phenylpropionic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be incorporated into the development of new drugs, enhancing the range of treatments available for different medical conditions.
Used as a Chiral Building Block:
In the chemical industry, (2R)-2-chloro-3-phenylpropionic acid serves as a chiral building block, which is essential for the production of various enantioselective compounds. Its specific stereochemistry is crucial for creating molecules with desired biological activities and properties.
Used in Organic Chemistry Research:
(2R)-2-chloro-3-phenylpropionic acid is utilized in organic chemistry research to explore new reactions and develop innovative synthetic pathways. Its reactivity and structural features make it a valuable compound for advancing the understanding of organic reactions and mechanisms.
Used in Antibacterial Applications:
Due to its potential antibacterial properties, (2R)-2-chloro-3-phenylpropionic acid is studied for use as an antibacterial agent. This could contribute to the development of new antibiotics to combat resistant bacteria and improve public health.
Used in Anti-inflammatory Applications:
(2R)-2-chloro-3-phenylpropionic acid is also being investigated for its anti-inflammatory properties, which could lead to its use in the development of anti-inflammatory drugs. This would provide an alternative for treating inflammation-related conditions and diseases.

Upstream product

• 109-95-5 ethyl nitrite 
• 150-30-1 Phenylalanine 
• 16503-53-0 2-bromo-3-phenylpropanoic acid 
• 17849-62-6 2-chloro-3-phenylpropionitrile 
• 50259-09-1 2-(1-chloro-2-phenyl-ethyl)-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine 
• 63-91-2 L-phenylalanine 
• 100-39-0 benzyl bromide 
• 408504-95-0 (2R,3S)-3-bromo-2-chloro-3-phenylpropanoic acid 
• 705-61-3 S-phenylalanine 
• 76043-69-1 2,2-dichloro-3-phenylpropionaldehyde 
• 123-91-1 1,4-dioxane 
• 20312-36-1 L-3-phenyllactic acid 
• 1112-67-0 tetrabutyl-ammonium chloride 
• 501-52-0 3-Phenylpropionic acid 

Downstream Products

• 59200-36-1 methyl 2-chloro-3-phenylpropanoate 
• 18166-56-8 α-chloro-β-phenylpropionamide 
• 7497-19-0 (S)-2-chloro-3-phenyl-propionic acid ethyl ester 
• 117770-84-0 N-(2-chloro-3-phenylpropionyl)tryptophan methyl ester 
• 141734-77-2 (7S)-methyl 7-benzyl 1,3,4,5,6,7-hexahydro-6-oxopyrrolo<4,3,2-fg><3>benzazocine-4-carboxylate 
• 141734-77-2 (7R)-methyl 7-benzyl 1,3,4,5,6,7-hexahydro-6-oxopyrrolo<4,3,2-fg><3>benzazocine-4-carboxylate 
• 63458-19-5 N-(2-phenylethyl)-2-naphthylamine 
• 1190832-61-1 C₁₅H₁₅ClN₂O 
• 7474-06-8 (S)-2-chloro-3-phenyl-propionic acid 
• 7474-06-8 (2R)-2-chloro-3-phenylpropionic acid 
• 59200-36-1 methyl (S)-2-chloro-3-phenylpropanoate 
• 120710-95-4 (S)-2-chloro-3-phenylpropanoic acid chloride 
• 111505-46-5 tert-butyl (S)-2-chloro-3-phenylpropanoate 
• 57359-76-9 (2R)-2-(acetylthio)-3-phenylpropanoic acid 

Relevant academic research and scientific papers

Quantitation of phenylalanine and its trans-cinnamic, benzoic and hippuric acid metabolites in biological fluids in a single GC-MS analysis

We describe a sensitive, simple and convenient stable isotope dilution assay developed to study endogenous metabolism of administered stable isotope-labeled phenylalanine (Phe) in phenylketonuric (PKU) mice treated experimentally with phenylalanine ammoni

Substrate-Inspired Fragment Merging and Growing Affords Efficacious LasB Inhibitors

Extracellular virulence factors have emerged as attractive targets in the current antimicrobial resistance crisis. The Gram-negative pathogen Pseudomonas aeruginosa secretes the virulence factor elastase B (LasB), which plays an important role in the infection process. Here, we report a sub-micromolar, non-peptidic, fragment-like inhibitor of LasB discovered by careful visual inspection of structural data. Inspired by the natural LasB substrate, the original fragment was successfully merged and grown. The optimized inhibitor is accessible via simple chemistry and retained selectivity with a substantial improvement in activity, which can be rationalized by the crystal structure of LasB in complex with the inhibitor. We also demonstrate an improved in vivo efficacy of the optimized hit in Galleria mellonella larvae, highlighting the significance of this class of compounds as promising drug candidates.

A facile microwave assisted synthesis and structure elucidation of (3R)-3-alkyl-4,1-benzoxazepine-2,5-diones by crystallographic, spectroscopic and DFT studies

The use of microwave (MW) irradiation in organic synthesis has become increasingly popular within the pharmaceutical and academic arenas because it is a new enabling technology for drug discovery and development. It is a rapid way of synthesis, which involves faster reaction rates and high selectivity to conventional heating method of syntheses. The MW-assisted 7-exo-tet cyclization of N-acylanthranilic acids afforded (3R)-3-alkyl-4,1-benzoxazepines-2,5-diones in very short duration (20 min) with extraordinary high yields in comparison to conventional heating mode of synthesis. The method development, comparative yields of MW-assisted and thermal method of syntheses, crystallographic, spectroscopic and density functional theory (DFT) studies are reported herein. Four novel compounds with chemical formulas C10H9BrClNO3 5m, C19H19NO3 6e, C13H14ClNO3 6h and C12H11Br2NO3 6h were synthesized, validated by 1HNMR, 13CNMR, FT-IR, UVVis, EIMS spectroscopic techniques and confirmed by using single crystal X-ray diffraction (SC-XRD) study. The DFT and TDDFT calculations at B3LYP/6-311 + G(d,p) level of theory were performed for comparative analysis of spectroscopic data, optimized geometries, frontier molecular orbitals (FMOs), natural bond orbital (NBO) analysis and nonlinear optical (NLO) properties of 5m, 6e, 6h and 6o. Overall, experimental findings were supported nicely by corresponding DFT computed results. The NBO analysis confirmed that the presence of non-covalent interactions, hydrogen bonding and hyper- conjugative interactions are pivotal cause for the existence of 5m, 6e, 6h and 6o in the solid-state. NLO analysis showed that 5m, 6e, 6h and 6o have significant NLO properties as compared to prototype standard compound which disclosed their potential for technology related applications.

A Straightforward Homologation of Carbon Dioxide with Magnesium Carbenoids en Route to α-Halocarboxylic Acids

The homologation of carbon dioxide with stable, (enantiopure) magnesium carbenoids constitutes a valuable method for preparing α-halo acid derivatives. The tactic features a high level of chemocontrol, thus enabling the synthesis of variously functionalized analogues. The flexibility to generate magnesium carbenoids through sulfoxide-, halogen- or proton- Mg exchange accounts for the wide scope of the reaction. (Figure presented.).

Preparation method of alpha-chloro carboxylic acid

The invention discloses a preparation method of alpha-chloro carboxylic acid. According to the preparation method, amino acids are dissolved into hydrochloric acid to form a homogeneous solution; thenobtained homogeneous solution and a sodium nitrite water solution are simultaneously pumped into a mixing valve through an injection pump A and an injection pump B of a micro-channel reaction apparatus; after the solutions are fully mixed, the mixed solution is pumped into a micro reactor of the micro-channel reaction apparatus to carry out reactions at a constant flowing speed, and the flow-outliquid namely alpha-chloro carboxylic acid is collected. The provided method realizes the continuous production of alpha-chloro carboxylic acid; furthermore, the product quality is good, the operationis simple, the using amount of raw materials is little, the process is safe, the method is green and environmentally friendly, energy is saved, the efficiency is high, and thus the method is suitablefor industrial production.

Di(1-naphthyl) methanol ester of carboxylic acids for absolute stereochemical determination

The absolute stereochemistry of chiral carboxylic acids is determined as a di(1-naphthyl)methanol ester derivative. Computational scoring of conformations favoring either P or M helicity of the naphthyl groups, capable of exciton-coupled circular dichroic coupling, leads to a predicted stereochemistry for the derivatized carboxylic acids.

Synthesis and anti-parasitic activity of C-benzylated (N-arylcarbamoyl)alkylphosphonate esters

Unexpected substituent-dependent regioselectivty challenges in the synthesis of C-benzylated (N-arylcarbamoyl)phosphonate esters have been resolved. The C-benzylated N-furfurylcarbamoyl derivative showed low micromolar PfLDH inhibition, while one of the C-benzylated N-arylcarbamoyl analogues was active against Nagana Trypanosoma brucei parasites which are responsible for African trypanosomiasis in cattle.

Enantioselective organocatalytic synthesis of 2-oxopiperazines from aldehydes: Identification of the elusive epoxy lactone intermediate

An organocatalytic linchpin catalysis approach was envisaged to convert simple aldehydes into enantioenriched 2-oxopiperazines. A four-step reaction sequence (chlorination, oxidation, substitution, and cyclization) was developed and led to different substitution patterns in high yields and selectivities. The reaction mechanism was studied, and the previously elusive epoxy lactone intermediate was identified by HRMS.

Chiral Pool-Based Synthesis of Naphtho-Fused Isocoumarins

A variety of chiral derivatives of benzo[d]naphtho[1,2-b]pyran-6-one were prepared in a single step by Et3N-mediated condensation of homophthalic anhydride with different derivatives of (S)-amino acid chlorides at -5 °C by employing a chiral pool methodology. Chirality 27:951-957, 2015.

Chiron based synthesis of isocoumarins: Reactivity of α-substituted carboxylic acids

The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and α-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with α-chloroacids afforded asymmetric isocoumarins in high yield.