2-[[4-(Methylamino)benzoyl]amino]pentanedioic acid

Base Information

• Chemical Name: 2-[[4-(Methylamino)benzoyl]amino]pentanedioic acid
• CAS No.: 52980-68-4
• Molecular Formula: C13H16N2O5
• Molecular Weight: 280.28
• Hs Code.: 2924299090
• NSC Number: 138419
• ChEMBL ID: CHEMBL591443
• Mol file: 52980-68-4.mol

Synonyms:NSC-138419;2-[[4-(methylamino)benzoyl]amino]pentanedioic acid;NSC138419;CHEMBL591443;SCHEMBL5925511;2-(4-(methylamino)benzamido)pentanedioic acid;N-[4-(Methylamino)-benzoyl]-L-glutamic acid;A816490;2-[[4-(methylamino)phenyl]carbonylamino]pentanedioic acid;2-[[[4-(methylamino)phenyl]-oxomethyl]amino]pentanedioic acid

Chemical Property of 2-[[4-(Methylamino)benzoyl]amino]pentanedioic acid

Chemical Property:

• Vapor Pressure: 1.32E-14mmHg at 25°C
• Boiling Point: 586.6°C at 760 mmHg
• Flash Point: 308.6°C
• PSA: 115.73000
• Density: 1.367g/cm³
• LogP: 1.24000
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 280.10592162
• Heavy Atom Count: 20
• Complexity: 364

Purity/Quality:

97% ^*data from raw suppliers

N-[4-(Methylamino)benzoyl]-L-glutamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=CC=C(C=C1)C(=O)NC(CCC(=O)O)C(=O)O
• Uses: N-[4-(Methylamino)benzoyl]-L-glutamic Acid acts as an inhibitor of human DNA methyltransferase.

Technology Process of 2-[[4-(Methylamino)benzoyl]amino]pentanedioic acid

There total 8 articles about 2-[[4-(Methylamino)benzoyl]amino]pentanedioic acid 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: 73.0%

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + p-(monomethylamino)benzoyl azide → p-(N-methylamino)benzoyl-L-glutamic acid (52980-68-4)

Guidance literature:

With 1,1,3,3-tetramethylguanidine; In dimethyl sulfoxide; at 25 ℃; for 1h;

DOI:10.1021/ja971568j

Reference yield:

N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid (59-05-2) → 2,4-diamino-6-(hydroxymethyl)pteridine (945-24-4) + p-(N-methylamino)benzoyl-L-glutamic acid (52980-68-4)

Guidance literature:

In phosphate buffer; pH=7.8; Product distribution; Irradiation;

DOI:10.1562/0031-8655(2002)076<0467:POMPPW>2.0.CO;2

Reference yield:

3-[3-((allyloxy)carbonyl)-5-oxo-1,3-oxazolan-4-yl]propanoic acid (138965-46-5) → p-(N-methylamino)benzoyl-L-glutamic acid (52980-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium / 0 °C

1.2: 1 h / 0 °C

1.3: 79 percent / conc. HCl / 0 °C / pH 1

2.1: 100 percent / diethylamine / palladium tetrakistriphenylphosphine / CH₂Cl₂ / 3 h / 20 °C

3.1: 73 percent / tetramethylguanidine / dimethylsulfoxide / 1 h / 25 °C

With 1,1,3,3-tetramethylguanidine; sodium; diethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; dimethyl sulfoxide; 1.1: Metallation / 1.2: Addition / 1.3: Hydrolysis / 2.1: deallylation / 3.1: Acylation;

DOI:10.1021/ja971568j

upstream raw materials:

N-(4-iodo-benzoyl)L-glutamic acid

methylamine

L-glutamic acid

(S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid

Downstream raw materials:

N¹⁰-methylfolic acid

N-{4-[(2-amino-4-dimethylamino-pteridin-6-ylmethyl)-methyl-amino]-benzoyl}-L-glutamic acid

N-(4-{[(Ξ)-1-(2,4-diamino-pteridin-6-yl)-ethyl]-methyl-amino}-benzoyl)-L-glutamic acid

N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid