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

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

Used in Pharmaceutical Synthesis:
Phthaloylgly Cylglycine is used as an intermediate in the synthesis of Rilmazafone Hydrochloride (R509715) for [application reason] its role in the production of a compound used in biological studies and as a sleep aid medication.
Used in Sleep Aid Medication:
Phthaloylgly Cylglycine is used as a component in the development of sleep aid medications, contributing to [application reason] its involvement in the synthesis of Rilmazafone Hydrochloride, which has potential applications in improving sleep quality and addressing sleep-related issues.
Used in Biological Studies:
Phthaloylgly Cylglycine is used as a component in the study of nitrazepam or rilmazafone hydrochloride combined with ethanol effects on human memory, playing a role in [application reason] its contribution to the synthesis of Rilmazafone Hydrochloride, which is essential for understanding the impact of these substances on cognitive functions.

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

Downstream Products

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

Application of remote photocyclization with a pair system of phthalimide and methylthio groups. A photochemical synthesis of cyclic peptide models

Application of regioselective remote photocyclization of a pair system consisting of a phthalimide group and a methylthio group to a homologous series of N-substituted phthalimides (4 and 5) possessing a terminal sulfide function in the amide side chain was investigated. On irradiation, medium to large membered cyclic peptide-like compounds (6, 7 and 9), up to a thirty-eight membered ring product (6f), were synthesized in moderate yields.

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.