1205-08-9

Usage

Uses

Used in Pharmaceutical Industry:
BENZOYLGLYCINE METHYL ESTER is used as a chemical intermediate for the synthesis of heteroaromatic inhibitors of astacin proteinases. These inhibitors play a crucial role in the development of novel therapeutic agents targeting various diseases and conditions.
Used in Research and Development:
In the field of research and development, BENZOYLGLYCINE METHYL ESTER serves as a valuable compound for studying the structure and function of various proteins, particularly those involved in enzymatic reactions. Its unique chemical properties make it a useful tool for understanding the mechanisms of protein-protein interactions and the development of new drugs targeting specific proteinases.
Used in Chemical Synthesis:
BENZOYLGLYCINE METHYL ESTER can be utilized as a key building block in the synthesis of various complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatile structure allows for further functionalization and modification, making it a valuable component in the development of new and innovative products.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 2605, 1948 DOI: 10.1021/ja01187a515Tetrahedron, 31, p. 2659, 1975 DOI: 10.1016/0040-4020(75)80328-0

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

Upstream product

• 186581-53-3 diazomethane 
• 495-69-2 Hippuric Acid 
• 67-56-1 methanol 
• 2979-64-8 hippuroylmercapto-acetic acid 
• 2403-55-6 4-(2-methyl-1-propenyl)morpholine 
• 119072-55-8 tert-butylisonitrile 
• 6639-62-9 methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide 
• 150-60-7 dibenzyl disulphide 
• 101649-82-5 N-benzoyl-2-bromoglycine methyl ester 
• 110-06-5 di-tert-butyl disulfide 
• 21286-78-2 methyl N-benzoyl-2-methoxyglycinate 
• 13079-28-2 benzoic toluene-p-sulphonic anhydride 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 58655-77-9 Tributyl(cyclopent-2-enyl)stannane 

Downstream Products

• 40527-16-0 5-methoxy-2-phenyloxazole 
• 5813-81-0 hippuramide 
• 104-63-2 N-Benzylethanolamine 
• 72085-01-9 N-2-(2-hydroxyethylamino)-2-oxoethylbenzamide 
• 1199-01-5 2-phenylazlactone 
• 53386-64-4 methyl 2-(benzylamino)acetate 
• 4172-41-2 hippuroyl-guanidine 
• 21286-78-2 methyl N-benzoyl-2-methoxyglycinate 
• 125700-10-9 α,α-dimethoxy-N-benzoyl-glycine methyl ester 
• 101823-13-6 methyl 2-(benzoylamino)hexanoate 
• 128590-72-7 diethyl N-<(methoxycarbonyl)methyl>benzimidoyl phosphite 
• 128590-74-9 [Benzoyl-(diethoxy-phosphanyl)-amino]-acetic acid methyl ester 
• 258505-90-7 (+/-)-dimethyl-2,3-dibenzamidobutanedioate 
• 158221-54-6 N-benzoyl-α-benzyldithioglycine methyl ester 

Relevant academic research and scientific papers

Homogeneous catalytic aminocarbonylation of iodoalkenes and iodobenzene with amino acid esters under conventional conditions and in ionic liquids

Amino acid methyl esters were used as amine nucleophiles in palladium catalysed aminocarbonylation of iodobenzene and iodoalkenes (1-iodo-cyclohexene and 17-iodo-androst-16-ene). 2-Oxo-carboxamide type derivatives can be isolated as a result of double CO insertion by using iodobenzene as a substrate at elevated carbon monoxide pressure. On the contrary, carboxamides of expected structure were obtained exclusively in excellent yields in the whole pressure range by using iodoalkenes. The aminocarbonylation of 17-iodo-androst-16-ene in [bmim][PF6] or [bmim][BF4] (where bmim=1-butyl-3-methyl- imidazolium cation) ionic liquids was also carried out and the ionic liquid-catalyst mixtures have been reused several times with only a small loss of activity.

Synthesis and docking studies of N-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamide analogues as potential alkaline phosphatase inhibitors

A series of N-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamides 6a–i were synthesized as alkaline phosphatase inhibitors. The intermediate 5-substituted 1,3,4-oxadiazole-2-thione 4 was synthesized starting with hippuric acid. Hippuric acid in the first step was converted into corresponding methyl ester 2 which upon reaction with hydrazine hydrate furnished the formation of hydrazide 3. The hippuric acid hydrazide was then cyclized into 5-substituted 1,3,4-oxadiazole-2-thione 4. The intermediate 4 was then reacted with alkyl or aryl halides 5a–5i to afford the title compounds N-(5-(methylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamides 6a–i. The bioassay results showed that compounds 6a–i exhibited good to excellent alkaline phosphatase inhibitory activity. The most potent activity was exhibited by the compound 6i having IC50 value 0.420 μM, whereas IC50 value of standard (KH2PO4) was 2.80 μM. Molecular docking studies was performed against alkaline phosphatase enzyme (PDBID 1EW2) to check binding affinity of the synthesized compounds 6a–i against target protein. The docking results showed that three compounds 6c, 6e, and 6i have maximum binding interactions with binding energy values of ?8 kcal/mol. The compound 6i displayed the interactions of oxadiazole ring nitrogen with amino acid His265 having a binding distance 2.13 ?. It was concluded from our results that synthesized compounds, especially compound 6i may serve as lead structure to design more potent inhibitors of human alkaline phosphatase.

Hydro-de-phosphoniation of 4-substituted-4-triphenylphosphonio-5(4H)-oxazolones with hydrogen iodide

4-Substituted-4-triphenylphosphonio-5(4H)-oxazolones, when reacted with hydrogen iodide in methylene chloride at room temperature, undergo hydro-de-phosphoniation to 5(4H)-oxazolonium salts, which react with methanol and triethylamine to give the correspo

Stabilization of the Max Homodimer with a Small Molecule Attenuates Myc-Driven Transcription

The transcription factor Max is a basic-helix-loop-helix leucine zipper (bHLHLZ) protein that forms homodimers or interacts with other bHLHLZ proteins, including Myc and Mxd proteins. Among this dynamic network of interactions, the Myc/Max heterodimer has

2-CHLORO-4,6-DISUBSTITUTED-1,3,5,-TRIAZINES A NOVEL GROUP OF CONDENSING REAGENTS

The title compounds form in reaction with carboxylic acids highly reactive intermediates, which are useful as acylating reagents in the preparation of esters, amides, acid anhydrides, and peptides in 64-98 percent yield.

Preparation method of carboxylic ester compound

The invention relates to a preparation method of a carboxylic ester compound, which comprises the following steps: reacting carboxylic acid with methanol in air under the catalysis of nitrite to obtain an ester compound, the preparation method disclosed by the invention has the advantages of rich raw material sources, cheap and easily available catalyst, mild reaction conditions, simplicity and convenience in operation and the like, a series of fatty carboxylic acids can be modified with high yield, and particularly, the traditional esterification method is generally not suitable for esterification of drug molecules. By utilizing the method, a series of known drug molecules can be modified, so that a shortcut is provided for discovering new drug molecules.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.

Visible-Light-Driven Oxidation of N -Alkylamides to Imides Using Oxone/H 2 O and Catalytic KBr

Imides are prepared conveniently by visible-light-driven oxidations of various N -alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H 2 O/CH 2 Cl 2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.