N-Phthaloylglycine

Base Information

• Chemical Name: N-Phthaloylglycine
• CAS No.: 4702-13-0
• Molecular Formula: C10H7NO4
• Molecular Weight: 205.17
• Hs Code.: 29251900
• European Community (EC) Number: 225-177-3
• NSC Number: 29044,10771
• UNII: 6J5LY4N0CG
• DSSTox Substance ID: DTXSID00197005
• Nikkaji Number: J68.615H
• Wikidata: Q27264991
• Pharos Ligand ID: 9DL69TFXW82A
• ChEMBL ID: CHEMBL2429920
• Mol file: 4702-13-0.mol

Synonyms:N-phthalylglycine;phthaloyl glycine

Chemical Property of N-Phthaloylglycine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.51E-07mmHg at 25°C
• Melting Point: 195-198 °C
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 412.6 °C at 760 mmHg
• PKA: 3.61±0.10(Predicted)
• Flash Point: 203.3 °C
• PSA: 74.68000
• Density: 1.522 g/cm³
• LogP: 0.30510
• Storage Temp.: 0-6°C
• Solubility.: DMSO, Methanol
• Water Solubility.: insoluble
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 205.03750770
• Heavy Atom Count: 15
• Complexity: 301

Purity/Quality:

99% ^*data from raw suppliers

N-Phthaloylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CC(=O)O
• Uses: N-Phthaloylglycine (cas# 4702-13-0) is a compound useful in organic synthesis.

Technology Process of N-Phthaloylglycine

There total 30 articles about N-Phthaloylglycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

phthalic anhydride (85-44-9) + glycine (56-40-6,18875-39-3,25718-94-9) → N-phthaloylglycine (4702-13-0)

Guidance literature:

for 0.0472222h; microwave irradiation;

Reference yield: 97.0%

tert-butyl 2-(1,3-dioxoisoindolin-2-yl)acetate (6297-93-4) → N-phthaloylglycine (4702-13-0)

Guidance literature:

With phosphoric acid; In toluene; at 50 ℃; for 2h;

DOI:10.1021/jo061377b

Reference yield: 95.0%

N-(2-Hydroxyethyl)phthalimide (3891-07-4) → N-phthaloylglycine (4702-13-0)

Guidance literature:

With ruthenium trichloride; sodium periodate; In ethyl acetate; acetonitrile; at 20 ℃; for 2h;

DOI:10.1080/00397919908086465

upstream raw materials:

phthalic anhydride

glycine

N-(2-Hydroxyethyl)phthalimide

N-(cyanomethyl)phthalimide

Downstream raw materials:

N,N-phthaloyl-glycine-(N-diphenylacetyl-p-toluidide)

N,N-phthaloyl-glycine-(N'-benzyloxycarbonyl-hydrazide)

(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid phenyl ester

Pht-Gly-Gly-OEt

Refernces

Synthesis of structurally diverse 2-azetidinones via staudinger reaction on a solid support

10.1246/bcsj.20100212

The research focuses on the synthesis of structurally diverse 2-azetidinones, which are key structural elements in the family of β-lactam antibiotics and possess significant biological activities. The study aims to develop a new method for the synthesis of β-lactams via ketene-imine cycloaddition using polymer-supported ketene on a solid support, specifically Merrifield resin. The researchers successfully synthesized a variety of β-lactam derivatives with different substituents at positions 1 and 4, which could serve as potential intermediates for the synthesis of active compounds. The process involved the use of trimellitic anhydride, phthaloylglycine, imines, Vilsmeier reagent, triethylamine, trifluoroacetic acid, methylhydrazine, and other reagents. The conclusions of the research highlight the selective cleavage of supported β-lactams by trifluoroacetic acid and methylhydrazine to obtain 4-carboxyphthalimido- and 3-amino-β-lactams, respectively. The method offers simplified purification through filtration, avoiding time-consuming separation techniques, and the ability to regenerate the starting polymer-supported phthaloylglycine, making it a valuable contribution to solid-phase polymer-supported synthesis.