5397-14-8

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl N-(4-chlorophenyl)-2-oxoglycinate is used as a synthetic intermediate for the development of pharmaceuticals. Its role in the synthesis of biologically active compounds makes it a valuable component in creating new medications.
Used in Agrochemical Production:
In the agrochemical sector, ethyl N-(4-chlorophenyl)-2-oxoglycinate is employed as a key intermediate in the production of various agrochemicals, contributing to the development of products that enhance crop protection and management.
Used in Research and Development:
Ethyl N-(4-chlorophenyl)-2-oxoglycinate is utilized as a reagent in organic synthesis within research and development settings. Its application in these environments facilitates the exploration and creation of novel chemical compounds and methodologies.

InChI:InChI=1/C10H10ClNO3/c1-2-15-10(14)9(13)12-8-5-3-7(11)4-6-8/h3-6H,2H2,1H3,(H,12,13)

Upstream product

• 106-47-8 4-chloro-aniline 
• 95-92-1 oxalic acid diethyl ester 
• 16717-44-5 α-anti(phenyl)-Fluorimino-(4-chlor-phenyl)-essigsaeureethylester 
• 2009-97-4 ethyl 2-diazo-3-oxobutanoate 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 324758-00-1 N-(p-Chlorphenyl)-aminofumarsaeureethylester 
• 4755-77-5 Ethyl oxalyl chloride 

Downstream Products

• 6333-34-2 NN'-(4,4'-dichlorodiphenyl)oxamide 
• 35551-24-7 4,4'-dimethoxy-benzilic acid-(4-chloro-anilide) 
• 17738-73-7 (4-chloro-phenyl)-oxalamide 
• 1338471-32-1 (S)-3-[(4-chloro-phenylaminooxalyl)-amino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid 
• 1349902-37-9 C₂₃H₃₂ClN₃O₂ 
• 1211293-87-6 C₂₀H₂₂ClN₃O₂ 
• 1253393-96-2 N₁-(4-chlorophenyl)-N₂-(piperidin-4-yl)oxalamide 
• 1349902-30-2 N₁-(1-carbamimidoylpiperidin-4-yl)-N₂-(4-chlorophenyl)oxalamide 
• 1349902-32-4 N₁-(1-carbamothioylpiperidin-4-yl)-N₂-(4-chlorophenyl)oxalamide 
• 1349902-33-5 N₁-(1-carbamoylpiperidin-4-yl)-N₂-(4-chlorophenyl)oxalamide 
• 1349902-34-6 N₁-(4-chlorophenyl)-N₂-(1-(phenylcarbamoyl)piperidin-4-yl)oxalamide 
• 1349902-35-7 N₁-(1-benzoylpiperidin-4-yl)-N₂-(4-chlorophenyl)oxalamide 
• 903055-93-6 C₁₄H₁₀BrClN₂O₂ 

Relevant academic research and scientific papers

Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates

We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, and phosgene-free route includes the generation of an isocyanate intermediate in situ via anodic decarboxylation of an oxamic acid in the presence of an organic base, followed by the one-pot addition of suitable nucleophiles to afford the corresponding ureas, carbamates, and thiocarbamates. This procedure is applicable to different amines, alcohols, and thiols. Furthermore, when single-pass continuous electrochemical flow conditions were used and this reaction was run in a carbon graphite Cgr/Cgr flow cell, urea compounds could be obtained in high yields within a residence time of 6 min, unlocking access to substrates that were inaccessible under batch conditions while being easily scalable.

Visible light-mediated photocatalytic oxidative cleavage of activated alkynes: Via hydroamination: A direct approach to oxamates

The direct oxidative cleavage of activated alkynes via hydroamination has been described using organic photocatalyst under visible-light irradiation at room temperature. In this reaction, the single electron oxidation of an in situ formed enamine followed by radical coupling with an oxidant finally delivers the oxamate. The key features of this photocatalytic reaction are the mild reaction conditions, metal-free organic dye as a photocatalyst, and TBHP playing a dual role as O source and for the regeneration of the photocatalyst.

Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase

Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development. We recently described a series of oxalic acid diamides that are converted into active SCD inhibitors within a subset of cancers by CYP4F11-mediated metabolism. Herein, we describe the optimization of the oxalic acid diamides and related N-acyl ureas and an analysis of the structure-activity relationships related to metabolic activation and SCD inhibition.

Metal-Free Oxidative C=C Bond Cleavage of Electron-Deficient Enamines Promoted by tert -Butyl Hydroperoxide

A novel tert -butyl hydroperoxide (TBHP)-promoted oxidative C=C double-bond cleavage of enamines is described. Heating a solution of an electron-deficient enamine in chlorobenzene at 80 °C in the presence of TBHP for two hours led to cleavage of the C=C bond. This study offers a new strategy to carry out C=O double-bond formation by the use of TBHP.

Structural insight into the reaction mechanism of Pd-catalyzed nitrile hydration: Trapping the [Pd(H2O)4]2+cation through a supramolecular complex

Four new bis(oxamato)palladate(II) complexes of formula (n-Bu4N)2[Pd(2,4,6-Me3pma)2]·2CH3CN (1), (n-Bu4N)2[Pd(2,4,6-Me3pma)2]·2CH3CONH2(2) and (n-Bu4N)4[Pd(H2O)4][Pd(4-Xpma)2]3·2CH3CONH2with X?=?Br (3) and Cl (4) (2,4,6-Me3pma?=?N-2,4,6-trimethylphenyloxamate, 4-Brpma?=?N-4-bromophenyloxamate, N-4-chlorophenyloxamate and n-Bu4N+?=?tetra-n-butylammonium) have been obtained and characterized by single crystal X-ray diffraction. All of them contain bis(oxamato)palladate(II) anions and bulky n-Bu4N+cations, but compounds 3 and 4 have also the out of the ordinary [Pd(H2O)4]2+inorganic cation. Acetonitrile and appealing acetamide are present as lattice molecules in compounds (1) and (2–4), respectively. While 1 was prepared in a neutral solution, species 2–4 were obtained in a basic medium. The acetamide molecules are the natural consequence of the acetonitrile hydration reaction during the oxamate-palladate(II) complexation. Interestingly, the use of a different oxamate ligand supports (through a molecular-recognition interaction) the structural grasping of the [Pd(H2O)4]2+species, which can be considered as a reaction intermediate for the nitrile hydration.

METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY

Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.

2,2,2-Trifluoroethyl Chlorooxoacetate-Universal Reagent for One-Pot Parallel Synthesis of N1-Aryl-N2-alkyl-Substituted Oxamides

A one-pot parallel synthesis of N1-aryl-N2-alkyl-substituted oxamides with 2,2,2-trifluoroethyl chlorooxoacetate was developed. The synthesis of a library of 45 oxamides revealed higher efficiency of this reagent over the known ethyl chlorooxoacetate. The reagent was successfully used to prepare the known oxamide-containing HIV entry inhibitors.

A transformation of N-alkylated anilines to N-aryloxamates

Transformation of N-alkylated anilines to N-aryloxamates was studied using ethyl 2-diazoacetoacetate as an alkylating agent and dirhodium tetraacetate (Rh2(OAc)4) as the catalyst. The general applicability of the reaction as a synthetic method for N-aryloxamates was studied with a number of substituted N-alkylated anilines. The results revealed that the oxamate was formed by a radical reaction with molecular O2 and Rh 2(OAc)4 as initiator. Copyright

New Highlights in the Synthesis of 4-Aryl-1,4-dihydropyrazines

The 4-aryl-1,4-dihydropyrazines were prepared via the cyclization of N,N-bisalkylated anilines with ammonium acetate. These reactions were aided by improvements in the synthesis of N,N-bisalkylated anilines which were alkylated with anilines using ethyl 2-diazo acetoacetate in a reaction catalyzed by rhodium acetate in the absence of oxygen. A possible mechanistic route is postulated on the basis of the isolation of the N-alkylation intermediates, which were determined to be N-aryloxamates by 1H NMR data and X-ray diffraction.

Design, synthesis, and antiviral activity of entry inhibitors that target the CD4-binding site of HIV-1

The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next- generation therapeutics and microbicides against HIV-1.