N-methyl-L-glutamic acid dibenzyl ester

Base Information

• Chemical Name: N-methyl-L-glutamic acid dibenzyl ester
• CAS No.: 146963-41-9
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• DSSTox Substance ID: DTXSID401225697
• Mol file: 146963-41-9.mol

Synonyms:N-methyl-L-glutamic acid dibenzyl ester;SCHEMBL23901485;DTXSID401225697;AM9167;146963-41-9;1,5-dibenzyl (2S)-2-(methylamino)pentanedioate;L-Glutamic acid, N-methyl-, bis(phenylmethyl) ester

Chemical Property of N-methyl-L-glutamic acid dibenzyl ester

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 401

Purity/Quality:

99.00% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CNC(CCC(=O)OCC1=CC=CC=C1)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CN[C@@H](CCC(=O)OCC1=CC=CC=C1)C(=O)OCC2=CC=CC=C2

Technology Process of N-methyl-L-glutamic acid dibenzyl ester

There total 4 articles about N-methyl-L-glutamic acid dibenzyl ester 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: 51.0%

N-methyl-N-(o-nitrobenzyl)-L-glutamic acid dibenzyl ester (146963-40-8) → N-methyl-L-glutamic acid dibenzyl ester (146963-41-9)

Guidance literature:

In 1,4-dioxane; for 1h; Irradiation;

DOI:10.1021/jo00058a049

Reference yield:

L-glutamic acid dibenzyl ester hydrochloride (4561-10-8) → N-methyl-L-glutamic acid dibenzyl ester (146963-41-9)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / tetrahydrofuran / 2 h

2: NaBH₃CN, acetic acid / dimethylsulfoxide / 3 h

3: 2) NaBH₃CN, acetic acid / 1) CH₃CN, water, 10 min, 2) 3 h

4: 51 percent / dioxane / 1 h / Irradiation

With sodium cyanoborohydride; acetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; dimethyl sulfoxide;

DOI:10.1021/jo00058a049

Reference yield:

(S)-2-{[1-(2-Nitro-phenyl)-meth-(E)-ylidene]-amino}-pentanedioic acid dibenzyl ester (146963-43-1) → N-methyl-L-glutamic acid dibenzyl ester (146963-41-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₃CN, acetic acid / dimethylsulfoxide / 3 h

2: 2) NaBH₃CN, acetic acid / 1) CH₃CN, water, 10 min, 2) 3 h

3: 51 percent / dioxane / 1 h / Irradiation

With sodium cyanoborohydride; acetic acid; In 1,4-dioxane; dimethyl sulfoxide;

DOI:10.1021/jo00058a049

upstream raw materials:

N-methyl-N-(o-nitrobenzyl)-L-glutamic acid dibenzyl ester

L-glutamic acid dibenzyl ester hydrochloride

(S)-2-{[1-(2-Nitro-phenyl)-meth-(E)-ylidene]-amino}-pentanedioic acid dibenzyl ester

N-(o-nitrobenzyl)-L-glutamic acid dibenzyl ester

Downstream raw materials:

N-methyl-L-2-oxopyrrolidine-5-carboxylic acid benzyl ester

(2S)-1-methyl-5-oxopyrrolidine-2-carboxylic acid