69555-14-2

Basic information

• Product Name: Ethyl N-(diphenylmethylene)glycinate
• Synonyms: (N,N-DIPHENYLMETHYLENE)GLYCINE ETHYL ESTER;N-(DIPHENYLMETHYLENE)GLYCINE ETHYL ESTER;ETHYL N-(DIPHENYLMETHYLENE)GLYCINATE;ETHYL (N-DIPHENYMETHYLENE)GLYCINATE;ETHYL (DIPHENYLMETHYLENAMINO)ACETATE;DIPHENYLMETHYLENE-GLYCINE ETHYL ESTER;AURORA KA-6707;Ethyl N-benzhydrylideneglycinate
• CAS NO: 69555-14-2
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 267.32
• EINECS: 1592732-453-0
• Product Categories: Amino Acids;Miscellaneous;Intermediates;Triazoles
• Mol File: 69555-14-2.mol

Chemical Properties

• Melting Point: 51-53 °C(lit.)
• Boiling Point: 195°C/2mmHg(lit.)
• Flash Point: >110°C
• Appearance: White to light yellow/Crystalline Powder or Crystals
• Density: 1.0690 (rough estimate)
• Vapor Pressure: 2.65E-05mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.22±0.50(Predicted)
• Sensitive: Moisture Sensitive
• Stability: Moisture Sensitive
• BRN: 1979922
• CAS DataBase Reference: Ethyl N-(diphenylmethylene)glycinate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl N-(diphenylmethylene)glycinate(69555-14-2)
• EPA Substance Registry System: Ethyl N-(diphenylmethylene)glycinate(69555-14-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37-26
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 69555-14-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl N-(diphenylmethylene)glycinate is used as a reagent for the synthesis of pyrazolopyrrolyl tetrahydropyran DPP-4 inhibitors. These inhibitors are important in the development of drugs for the treatment of type 2 diabetes, as they help to increase the levels of insulin in the body and improve glucose control.
Used in Chemical Synthesis:
Ethyl N-(diphenylmethylene)glycinate is also used as a versatile reagent in the synthesis of various chemical compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows it to participate in a wide range of reactions, making it a valuable building block in organic chemistry.

InChI:InChI=1/C17H17NO2/c1-2-20-16(19)13-18-17(14-9-5-3-6-10-14)15-11-7-4-8-12-15/h3-12H,2,13H2,1H3

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 1013-88-3 Benzophenone imine 
• 623-33-6 glycine ethyl ester hydrochloride 
• 97611-55-7 ethyl 2-acetoxy-2-diphenylmethyleneaminoacetate 
• 119-61-9 benzophenone 
• 930299-14-2 ethyl (S_S,2R,3S)-(+)-2-N-(diphenylmethyleneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate 
• 749253-91-6 (S_S,2S,3S)-(+)-ethyl 2-N-(diphenylmethylideneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate 
• 459-73-4 GlyOEt*HCl 
• 100-59-4 phenylmagnesium chloride 
• 100-47-0 benzonitrile 
• 51-79-6 urethane 

Downstream Products

• 130558-78-0 2,2-Diphenyl-5-[1-phenyl-meth-(Z)-ylidene]-2,5-dihydro-oxazole-4-carboxylic acid ethyl ester 
• 616-06-8 2-amino-hexanoic acid 
• 142348-48-9 ethyl N-(diphenylmethylene)-4-(bromomethyl)-D,L-phenylalaninate 
• 126861-99-2 2-(Benzhydrylidene-amino)-butyric acid ethyl ester 
• 130558-74-6 5-[1-Chloro-meth-(E)-ylidene]-2,2-diphenyl-2,5-dihydro-oxazole-4-carboxylic acid ethyl ester 
• 142229-07-0 (2RS,3SR) ethyl 2-diphenylmethyleneimino-4-nitro-3-phenylbutanoate 
• 140483-35-8 (Benzhydrylidene-amino)-(4-oxo-4H-chromen-2-yl)-acetic acid ethyl ester 
• 156393-78-1 2-(Benzhydrylidene-amino)-4-(dimethoxy-phosphoryl)-butyric acid ethyl ester 
• 137283-22-8 4-Benzenesulfinyl-2-(benzhydrylidene-amino)-butyric acid ethyl ester 
• 119-61-9 benzophenone 
• 136964-35-7 ethyl 4-cyclopropylidene-2-<(diphenylmethylene)imino>butanoate 
• 156143-60-1 4-[2-(Benzhydrylidene-amino)-2-ethoxycarbonyl-ethyl]-benzoic acid tert-butyl ester 
• 97612-01-6 Benzoic acid (benzhydrylidene-amino)-ethoxycarbonyl-methyl ester 
• 118553-14-3 2-(Benzhydrylidene-amino)-3-dimethylamino-propionic acid ethyl ester 

Relevant articles and documents

Formation and Reaction of Azomethine Ylide by the Reaction of Cu(acac)2ketocarbenoids with 1,1-Diphenylmethanimine

The reaction of α-diazacarbonyl compounds with 1,1-diphenylmethanimine in the presence of Cu(acac)2 afforded the corresponding N-substituted imines in general together with pyrrolidine and 1,4,6-dioxazocine derivatives (in the reaction of α-diazo-4-chloroacetophenone) and 1,1-diphenyl-2-(4-nitrobenzoyl)ethylene (in the reaction of α-diazo-4-nitroacetophenone) through azomethine ylides.

Synthetic route of lacosamide

The invention discloses a new synthesis route of lacosamide. The new synthesis route comprises the following steps: taking glycine ethyl ester hydrochloride as an initial raw material to react with methylbenzene, benzophenone and p-toluenesulfonic acid to obtain a compound of formula M1; reacting the compound of formula M1 with Xmethyl methyl ether to generate a compound of formula M2; reacting the compound of formula M2 with benzylamine under the catalytic action of sodium ethoxide to generate a compound of formula M3; reacting the compound of formula M3 under the action of acid to generate acompound of formula M4; reacting the compound of formula M4 with Ltartaric acid to generate a compound of formula M5; and enabling the compound of formula M5 to react with acetic anhydride to generate the lacosamide compound. The synthesis route has the advantages that the atom economy is high, the use of isopropyl chloroformate highly toxic products for preparing amide is avoided, the use of methylation reagents methyl iodide or dimethyl sulfate is avoided, the yield is high, and the like.

Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams

We report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory diastereoselectivities in most cases. This reaction also features good functional-group tolerance, facile scalability and product diversification. Experimental and computational studies suggest that α-ketoacylsilanes can serve as photochemical precursors by engaging in a 1,3 silicon shift to the distal carbonyl group.

Preparation method of benzophenone imine glycine ester

The invention relates to a preparation method of benzophenone imine glycine ester, and belongs to the technical field of chemical organic synthesis. The preparation method comprises the following step: by taking benzophenone imine as an initial raw material, reacting benzophenone imine with halogenated acetate in the presence of alkali to obtain benzophenone imine glycine ester. The structure of the halogenated acetate is shown as a formula 3 in the specification, wherein X is chlorine or bromine, and R is methyl, ethyl, isopropyl or tertiary butyl. By starting from simple and easily available raw materials, the invention provides a simple and convenient method for synthesizing benzophenone imine glycine ester.

Structure-based virtual screening for insect ecdysone receptor ligands using MM/PBSA

The ecdysone receptor (EcR) is an insect nuclear receptor that is activated by the molting hormone, 20-hydroxyecdysone. Because synthetic EcR ligands disrupt the normal growth of insects, they are attractive candidates for new insecticides. In this study, the Molecular Mechanics/Poisson–Boltzmann Surface Area (MM/PBSA) method was used to predict the binding activity of EcR ligands. Validity analyses using 40 known EcR ligands showed that the binding activity was satisfactorily predicted when the ligand conformational free energy term was introduced. Subsequently, this MM/PBSA method was applied to structure-based hierarchical virtual screening, and 12 candidate compounds were selected from a database of 3.8 million compounds. Five of these compounds were active in a cell-based competitive binding assay. The most potent compound is a simple proline derivative with low micromolar binding activity, representing a valuable lead compound for further structural optimization.

Enantio- and Diastereoselective Synthesis of β-Aryl-β-pyrazolyl α-Amino Acid Esters via Copper-Catalyzed Reaction of Azomethine Ylides with Benzylidenepyrazolones

A fully stereoselective synthesis of unnatural chiral β-aryl-β-pyrazolyl α-amino acid esters via copper-catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1H-pyrazol-5-ol was introduced by the aromatization of 3H-pyrazol-3-one in the reaction. The transformation operated at room temperature and afforded β-1H-pyrazol-5-ol-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.

Enantio- And diastereoselective synthesis of b-Aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed reaction of azomethine ylides with benzylidenepyrazolones

A fully stereoselective synthesis of unnatural chiral b-aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1H-pyrazol-5-ol was introduced by the aromatization of 3H-pyrazol-3-one in the reaction. The transformation operated at room temperature and afforded b-1H-pyrazol-5-ol-a-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.

CHEMICAL COMPOUNDS

The present disclosure relates to compounds of Formula (I): and to their pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein inhibit the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inter alia autoinflammatory and autoimmune diseases and cancers.

Preparation method of anti-heart-failure enkephalinase inhibitor sacubitril intermediate

The invention discloses a preparation method of an anti-heart-failure enkephalinase inhibitor sacubitril intermediate. The preparation method includes following steps: 1), in the presence of tetrahydropyrrole and a 4-angstrom molecular sieve, allowing glycine ethyl ester to have contact reaction with benzophenone to obtain glycine ethyl ester benzophenone imide; 2), in the presence of 8-hydroxyquinoline and organic alkali, allowing the glycine ethyl ester benzophenone imide to have temperature rise reflux reaction with 4-halogenated methyl biphenyl to obtain (R)-2-biphenyl methyl glycine ethylester benzophenone imide; 3), subjecting the (R)-2-biphenyl methyl glycine ethyl ester benzophenone imide obtained in the step 2) to stirring reaction under an acidic condition to obtain the intermediate (R)-2-biphenyl methyl glycine ethyl ester. The preparation method has the advantages that a chiral product is formed through chemical selection, the method is mild in condition, lower in cost andmore suitable for industrial application, and an important raw material source guarantee is provided for sacubitril or an anti-heart-failure drug Entresto.

Preparation method and application of high-optical-purity biphenylalanine and derivative thereof

The invention relates to a preparation method and application of high-optical-purity biphenylalanine and a derivative thereof. The preparation method employs an acidic resolution reagent and controls the pH value of a reaction so as to prepare a target compound. According to the invention, raw materials are simple, easily available and cheap; the product obtained after resolution has high optical purity, so the problem of a final product with high optical purity is hard to prepare through refining in the prior art; and the preparation method is simple to operate, high in security, and low in the usage amount of wastewater and energy consumption, can overcome EHS problems in drug development, and is suitable for industrial large-scale production.