3916-40-3

Basic information

• Product Name: Phthaloylgly Cylglycine
• Synonyms: Phthaloylgly Cylglycine;N-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl]glycine;[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)acetylamino]acetic acid;2-(2-Phthalimidoacetylamino)acetic acid;N-[[(Carboxymethyl)carbamoyl]methyl]phthalimide;2-[[2-(1,3-diketoisoindolin-2-yl)acetyl]amino]acetic acid;2-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]acetic acid;2-[2-(1,3-dioxoisoindol-2-yl)ethanoylamino]ethanoic acid
• CAS NO: 3916-40-3
• Molecular Formula: C₁₂H₁₀N₂O₅
• Molecular Weight: 262.2182
• EINECS: 223-481-0
• Mol File: 3916-40-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 583.9°Cat760mmHg
• Flash Point: 306.9°C
• Appearance: /
• Density: 1.509g/cm³
• Vapor Pressure: 1.78E-14mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: Phthaloylgly Cylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: Phthaloylgly Cylglycine(3916-40-3)
• EPA Substance Registry System: Phthaloylgly Cylglycine(3916-40-3)

Safety Data

• Hazardous Substances Data: 3916-40-3(Hazardous Substances Data)

Usage

Uses

N-Phthaloylglycylglycine is an intermediate used in the synthesis of Rilmazafone Hydrochloride (R509715), which can be used in biological study of nitrazepam or rilmazafone hydrochloride combined with ethanol effects on human memory. It is also used as sleep aid medication.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 1312, 1950 DOI: 10.1021/ja01159a066

InChI:InChI=1/C12H10N2O5/c15-9(13-5-10(16)17)6-14-11(18)7-3-1-2-4-8(7)12(14)19/h1-4H,5-6H2,(H,13,15)(H,16,17)

Upstream product

• 106-57-0 Glycine anhydride 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 78425-85-1 (N,N-phthaloyl-glycyl)-phosphoric acid dibenzyl ester 
• 56-40-6 glycine 
• 4702-13-0 N-phthaloylglycine 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 6780-38-7 N-phthaloylglycine chloride 
• 21313-49-5 N,N-phthaloyl-glycine-(4-nitro-phenyl ester) 
• 5033-17-0 methyl 2-(2-phthalimidoacetamido)acetate 
• 85-44-9 phthalic anhydride 
• 556-50-3 glycylglycine 
• 2641-02-3 Pht-Gly-Gly-OEt 

Downstream Products

• 59180-18-6 4-chloro-2-(o-chlorobenzoyl)-N-methyl-N^α-(phthalylglycyl)glycinanilide 
• 59180-37-9 N-({[4-Chloro-2-(2-fluoro-benzoyl)-phenyl]-methyl-carbamoyl}-methyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide 
• 74088-64-5 N-({[4-Chloro-2-(hydroxy-phenyl-methyl)-phenyl]-methyl-carbamoyl}-methyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide 
• 59180-33-5 4-chloro-2-(o-chloro-α-hydroxybenzyl)-N-methyl-N^α-(phthalylglycyl)glycinanilide 
• 59180-34-6 N-[({4-Chloro-2-[(2-fluoro-phenyl)-hydroxy-methyl]-phenyl}-methyl-carbamoyl)-methyl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide 
• 111411-64-4 N-(N,N-phthaloyl-glycyl)-glycine anilide 

Relevant articles and documents

Metal directed assemblies of a dipeptide: Formation of β-pleated sheets

The crystal structure of N-phthaloylglycylglycine and its complexes with copper(II) and zinc(II) are studied. The N-phthaloylglycylglycinato copper(II) complex has a polymeric structure formed by bridging carboxylates. The corresponding N-phthaloylglycylglycinato zinc(II) complex is monomeric. Both the metal complexes have self-assembled hydrogen-bonded structures in which dipeptide ligand adopt β-pleated conformations. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

A synthetic strategy for the preparation of cyclic peptide mimetics based on SET-promoted photocyclization processes

A novel method for the synthesis of cyclic peptide analogues has been developed. The general approach relies on the use of SET-promoted photocyclization reactions of peptides that contain N-terminal phthalimides as light absorbing electron acceptor moieties and C-terminal α-amidosilane or α-amidocarboxylate centers. Prototypical substrates are prepared by coupling preformed peptides with the acid chloride of N-phthalimidoglycine. Irradiation of these substrates results in the generation of cyclic peptide analogues in modest to good yields. The chemical efficiencies of these processes are not significantly affected by (1) the lengths of the peptide chains separating the phthalimide and α-amidosilane or α-amidocarboxylate centers and (2) the nature of the penultimate cation radical α-heterolytic fragmentation process (i.e., desilylation vs decarboxylation). An evaluation of the effects of N-alkyl substitution on the amide residues in the peptide chain showed that N-alkyl substitution does not have a major impact on the efficiencies of the photocyclization reactions but that it profoundly increases the stability of the cyclic peptide.