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
• Article Data: 36

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

N-(Diphenylmethylene)glycine Ethyl Ester is used as a reagent in the synthesis of pyrazolopyrrolyl tetrahydropyran DPP-4 inhibitors.

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

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

Downstream Products

• 138804-00-9 4-Cyan-2-N-(Diphenylmethylen)-3-phenylglutaminsaeurediethylester 
• 126862-00-8 ethyl N-(diphenylmethylene)-DL-(p-nitrophenyl)alaninate 
• 130558-73-5 2,2-diphenyl-5-dichloromethylene-3-oxazoline-4-ethylcarboxylate 
• 180608-82-6 ethyl 4-bromo-2-(2,2-diphenyl-1-azavinyl)pent-4-enoate 
• 171922-27-3 Ethyl N-(diphenylmethylene)-2,2-bis(2-bromoallyl)glycinate 
• 174003-91-9 (2R,1'R,2'R,4S)-ethyl N-diphenylmethylidene-2-<2'-<(4-benzyl-2-oxazolidinon-3-yl)carbonyl>-3',3'-difluoro>cyclopropylglycinate 
• 174969-99-4 2-(Benzhydrylidene-amino)-3-[4-(dimethoxy-phosphorylmethyl)-phenyl]-propionic acid ethyl ester 
• 174969-98-3 2-(Benzhydrylidene-amino)-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-propionic acid ethyl ester 
• 54011-41-5 α-Phenylacetylglycinaethylester 
• 214842-20-3 2-(Benzhydrylidene-amino)-3-(4-cyano-phenyl)-propionic acid ethyl ester 
• 75154-68-6 methyl (2S)-N-tritylaziridine-2-carboxylate 
• 167849-33-4 3',5'-di-tert-butyltyrosine ethyl ester 
• 677005-00-4 (R)-2-(Benzhydrylidene-amino)-3-naphthalen-1-yl-propionic acid ethyl ester 

Relevant articles and documents

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.

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.

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.