dimethyl N-(4-aminobenzoyl)-L-glutamate

Base Information

• Chemical Name: dimethyl N-(4-aminobenzoyl)-L-glutamate
• CAS No.: 52407-60-0
• Molecular Formula: C14H18N2O5
• Molecular Weight: 294.307
• DSSTox Substance ID: DTXSID70499503
• Wikidata: Q82350324
• Mol file: 52407-60-0.mol

Synonyms:52407-60-0;dimethyl N-(4-aminobenzoyl)-L-glutamate;N-(p-Aminobenzoyl)-L-glutamic Acid Dimethyl Ester;dimethyl (2S)-2-[(4-aminobenzoyl)amino]pentanedioate;L-Glutamic acid, N-(4-aminobenzoyl)-, dimethyl ester;Dimethyl (4-aminobenzoyl)-L-glutamate;SCHEMBL9483698;DTXSID70499503;KTNFJPQFZZYFPU-NSHDSACASA-N;AKOS030240683;1,5-dimethyl (2S)-2-[(4-aminophenyl)formamido]pentanedioate

Chemical Property of dimethyl N-(4-aminobenzoyl)-L-glutamate

Chemical Property:

• Boiling Point: 505.6±50.0 °C(Predicted)
• PKA: 13.66±0.46(Predicted)
• PSA: 107.72000
• Density: 1.234±0.06 g/cm3(Predicted)
• LogP: 1.46550
• Solubility.: DMSO. Methanol
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 294.12157168
• Heavy Atom Count: 21
• Complexity: 378

Purity/Quality:

99% ^*data from raw suppliers

N-(p-Aminobenzoyl)-L-glutamicAcidDimethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC(C(=O)OC)NC(=O)C1=CC=C(C=C1)N
• Isomeric SMILES: COC(=O)CC[C@@H](C(=O)OC)NC(=O)C1=CC=C(C=C1)N
• Uses: N-(p-Aminobenzoyl)-L-glutamic Acid Dimethyl Ester is an intermediate in the synthesis of Folic Acid (F680300), an vitamin needed to synthesize DNA, conduct DNA repair and methylate DNA by acting as a cofactor in biological reactions involving folate.

Technology Process of dimethyl N-(4-aminobenzoyl)-L-glutamate

There total 11 articles about dimethyl N-(4-aminobenzoyl)-L-glutamate 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: 81.5%

(S)-folic acid dimethylester benzenesulfonic acid → tetrahydrofolic acid dimethylester + dimethyl N-(4-amino-benzoyl)-L-glutamate (52407-60-0)

Guidance literature:

With daniphos chiral ligand; hydrogen; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In methanol; at 70 ℃; for 17h; under 60004.8 Torr; Further Variations:; ligand; Product distribution;

DOI:10.1016/j.jorganchem.2005.11.026

Reference yield:

C19H26N2O7 → N-(4-amino-benzoyl)-glutamic acid dimethyl ester (52407-60-0)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.ejmech.2020.112986

Reference yield:

methanol (67-56-1) + N-(4-aminobenzoyl)-L-glutamic acid (4271-30-1,532-63-8) → dimethyl N-(4-amino-benzoyl)-L-glutamate (52407-60-0)

Guidance literature:

With acetyl chloride;

DOI:10.1021/ja01554a047

upstream raw materials:

glutamic acid dimethyl ether

4-amino-benzoic acid

Glutamic acid

4-(N-tert-butoxycarbonyl)aminobenzoic acid

Downstream raw materials:

N-{4-[(2-oxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester

N-{4-[(2-thioxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester

N-{4-[(2-thioxo-benzothiazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester

N-{4-[(5-methoxycarbonyl-2-thioxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester