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 
• 100-47-0 benzonitrile 
• 100-59-4 phenylmagnesium chloride 
• 1013-88-3 Benzophenone imine 
• 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 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 616-06-8 2-amino-hexanoic acid 
• 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 
• 97611-55-7 ethyl 2-acetoxy-2-diphenylmethyleneaminoacetate 
• 82954-73-2 C₂₆H₃₁N₂O₃ 
• 156143-52-1 2-(Benzhydrylidene-amino)-3-(4-tert-butoxycarbonylmethyl-phenyl)-propionic acid ethyl ester 
• 138803-99-3 4-Ethoxycarbonyl-2-N-(Diphenylmethylen)-3-(4'-cyanphenyl)-glutaminsaeurediethylester 
• 156143-76-9 2-(Benzhydrylidene-amino)-3-(4-ethoxycarbonylmethyl-phenyl)-propionic acid ethyl ester 
• 133409-97-9 2-(Benzhydrylidene-amino)-3-(4-tert-butoxycarbonyloxy-2-difluoromethyl-phenyl)-propionic acid ethyl ester 
• 81477-96-5 ethyl α-<(diphenylmethylene)amino>-(+/-)-benzeneacetate 

Relevant articles and documents

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.

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.

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.