42013-20-7

Usage

Chemical Properties

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Uses

The main metabolite of o-xylene.

Definition

ChEBI: An N-acylglycine that is the ortho-methyl derivative of hippuric acid.

General Description

2-Methylhippuric acid is also known as o-methylhippuric acid and its determination in urine by gas chromatography was reported. It is the urinary metabolic biomarker for the diagnosis of human Hepatitis B virus.

InChI:InChI=1/C10H11NO3/c1-7-4-2-3-5-8(7)10(14)11-6-9(12)13/h2-5H,6H2,1H3,(H,11,14)(H,12,13)/p-1

Upstream product

• 933-88-0 ortho-toluoyl chloride 
• 56-40-6 glycine 
• 78973-74-7 N-o-toluoyl-glycine ethyl ester 

Downstream Products

• 78973-74-7 N-o-toluoyl-glycine ethyl ester 
• 72615-39-5 2-o-Tolyl-4-[1-o-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one 
• 72615-40-8 2-m-Tolyl-4-[1-o-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one 
• 376392-00-6 N-[2-(1,4-diazabicyclo[3.2.2]non-4-yl)-2-oxoethyl]-2-methylbenzamide 
• 1224962-86-0 C₁₂H₁₃NO₄ 
• 313645-46-4 4-(4-nitrobenzylidene)-2-(2-methylphenyl)-5(4H)-oxazolone 
• 313645-49-7 4-(4-methoxybenzylidene)-2-(2-methylphenyl)-5(4H)-oxazolone 
• 118-90-1 ortho-methylbenzoic acid 
• 1268528-43-3 C₆₃H₆₇N₁₇O₁₁ 
• 1361249-71-9 [(2-methylbenzoyl)amino]methyl acetate 
• 53949-13-6 (Z)-2-phenyl-4-(2-methylbenzylidene)-(4H)-1,3-oxazol-5-one 
• 72615-41-9 2-p-Tolyl-4-[1-o-tolyl-meth-(Z)-ylidene]-4H-oxazol-5-one 
• 1447964-05-7 (Z)-4-(2-(piperidin-1-yl)benzylidene)-2-o-tolyloxazol-5(4H)-one 

Relevant academic research and scientific papers

Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents

As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value of 4Bs was above 526, indicating the favorable safety profile. Interestingly, unlike nucleoside analogue 3TC, 4Bs could significantly inhibit 3.5 kb pgRNA expression. Molecular docking study revealed that 4Bs could fit well into the dimer-dimer interface of HBV core protein by hydrophobic, π–π and H-bond interactions. Considering the potent anti-HBV activity, low toxicity and diverse anti-HBV mechanism from that of nucleoside anti-HBV agent 3TC, compound 4Bs might be a promising lead to develop novel non-nucleoside anti-HBV therapeutic agents, and warranted further investigation.

Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates

Earth-abundant nickel, coordinated with a suitable chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2-amidoacrylates, affording the chiral α-amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted into chiral α-amino acids, β-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations.

Palladium-catalyzed ortho-arylation of benzoic acid derivatives via C-H bond activation using an aminoacetic acid bidentate directing group

A highly efficient protocol for the palladium-catalyzed ortho-arylation of benzoic acid derivatives by aryl iodides is described with an aminoacetic acid based N,O bidentate directing group. This protocol can be applied to various benzoyl aminoacetic acids and aryl iodides with both electron-donating and electron-withdrawing groups. Remarkably, the nature of a new directing group drives selective C-H bond activation to afford only monoarylation products in good to excellent yields.

Lewis acid catalyzed formation of 3-amino-3-carboxy-tetrahydroquinoline derivatives via tandem 1,5-hydride transfer/cyclization process

A Sc(OTf)3-catalyzed intramolecular tandem 1,5-hydride transfer/cyclization process to construct 3-amino-3-carboxy-tetrahydroquinoline derivatives has been developed. The methodology gives access to a range of relatively complex tetrahydroquinolines (tetracyclic and pentacyclic heterocycles bearing spirocyclic skeleton and two stereogenic centers) in good to excellent yields with diastereoselectivities ranging from 57:43 to 73:27. The synthetic utility of the method was also demonstrated by an efficient ring opening derivatization reaction.

Substituents effect on the erlenmeyer-ploechl reaction: Understanding an observed process reaction time

A systematic study on hippuric acid substituents was performed in order to better understand the influence of stereoelectronic factors on the Erlenmeyer reaction rate. In addition, two reaction systems were evaluated: Huenig's base solvent free conditions and catalytic sodium acetate in 2-methyl-THF. The effect on reaction rate of electron withdrawing and electron donating groups are reported. Specifically, the study led to the conclusion that stereoelectronic factors have significant influence in one of our key Erlenmeyer reaction by affecting its reaction rate.

A Chromogen Produced in the Reaction of Glycine Derivatives with Acetic Anhydride and Pyridine

The yellow chromogen produced in the assay of glutathione or glycocholic acid by their reactions with acetic anhydride and pyridine was found to be a conjugated compound containing pyridylidene and 2-oxazoline rings.The structure was confirmed by hydrolysis of the chromogen to 4-aminomethylpyridine.The same chromogen was formed with benzoylpeptides having C-terminal glycine.Keywords - chromogen; Glutathione; glycocholic acid; spectrophotometry; 2-oxazoline; pyridylidene