87766-32-3

Basic information

• Product Name: pyroglutamylbenzylamide
• Synonyms: pyroglutamylbenzylamide;(S)-5-Oxo-N-(phenylmethyl)-2α-pyrrolidinecarboxamide;N-Benzyl-5-oxopyrrolidine-2α-carboxamide
• CAS NO: 87766-32-3
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 0
• Mol File: 87766-32-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 555°C at 760 mmHg
• Flash Point: 244.6°C
• Appearance: /
• Density: 1.199g/cm³
• Vapor Pressure: 2.34E-12mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: pyroglutamylbenzylamide(CAS DataBase Reference)
• NIST Chemistry Reference: pyroglutamylbenzylamide(87766-32-3)
• EPA Substance Registry System: pyroglutamylbenzylamide(87766-32-3)

Safety Data

• Hazardous Substances Data: 87766-32-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H14N2O2/c15-11-7-6-10(14-11)12(16)13-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,13,16)(H,14,15)/t10-/m0/s1

Upstream product

• 16450-41-2 L-glutamic acid diethyl ester 
• 100-46-9 benzylamine 
• 98-79-3 L-Pyroglutamic acid 
• 14842-41-2 (S,S)-1,7-diazatricyclo[7.3.0.0^7,11]dodecane-2,6,8,12-tetrone 
• 511543-55-8 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione 
• 4931-66-2 methyl (S)-pyroglutamate 
• 56-86-0 L-glutamic acid 

Downstream Products

• 1266229-67-7 benzyl {(1S)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxo-1-phenylethyl}carbamate 
• 1266230-12-9 benzyl {(1S)-1-(4,4-difluorocyclohexyl)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxoethyl}carbamate 
• 1266230-03-8 benzyl [(1S)-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethyl]carbamate 
• 1266229-75-7 (3S,8aR)-2-[(2S)-2-amino-2-phenylacetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]octahydropyrrolo[1,2-a]pyrazine-3-carboxamide 
• 1266230-13-0 (3S,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]octahydropyrrolo[1,2-a]pyrazine-3-carboxamide 
• 1266229-74-6 tert-butyl [(1S)-2-({(1S)-2-[(3S,8aR)-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxo-1-phenylethyl}amino)-1-methyl-2-oxoethyl]methylcarbamate 
• 1266230-14-1 C₃₄H₄₉F₂N₅O₆ 
• 1266229-49-5 C₁₇H₂₄N₂O₂ 
• 1179348-77-6 (S)-2-benzylcarbamoyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 75773-76-1 (S)‐N‐benzyl‐1‐(pyrrolidin‐2‐yl) methanamine 
• 119766-85-7 (S)-1-(2-Chloro-acetyl)-5-oxo-pyrrolidine-2-carboxylic acid benzylamide 
• 119766-83-5 (S)-5-Oxo-1-propionyl-pyrrolidine-2-carboxylic acid benzylamide 
• 119766-86-8 (S)-1-Benzoyl-5-oxo-pyrrolidine-2-carboxylic acid benzylamide 
• 119766-82-4 (S)-1-Acetyl-5-oxo-pyrrolidine-2-carboxylic acid benzylamide 

Relevant articles and documents

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

Discovery of highly functionalized scaffolds: Pyrroloimidazolediones as P2X7 receptor antagonists

A broad range of pyrroloimidazolediones, new highly functionalized bicyclic heterocycles, was obtained by a cycloaddition reaction between L-pyroglutamide derivatives and Bredereck's reagent. Methanolysis of subsequent pyrroloimidazolediones provided antagonists of P2X7 receptor, with retention of initial stereoconfiguration, with potential applications in the treatment of inflammatory and neurological diseases. We have thus developed a new synthesis of lactamic nitrogen free enaminones which is currently the easiest method cited in the literature to access these compounds.

B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

The use of B(OCH2CF3)3 for mediating direct amidation reactions of a wide range of pharmaceutically relevant carboxylic acids and amines is described, including numerous heterocycle-containing examples. An initial screen of solvents for the direct amidation reaction suggested that cyclopentyl methyl ether, a solvent with a very good safety profile suitable for use over a wide temperature range, was an excellent replacement for the previously used solvent acetonitrile. Under these conditions amides could be prepared from 18 of the 21 carboxylic acids and 18 of the 21 amines examined. Further optimisation of one of the low yielding amidation reactions (36% yield) via a design of experiments approach enabled an 84% yield of the amide to be obtained.