Diethyl N-{2-chloro-4-[(prop-2-yn-1-yl)amino]benzoyl}-L-glutamate

Base Information

• Chemical Name: Diethyl N-{2-chloro-4-[(prop-2-yn-1-yl)amino]benzoyl}-L-glutamate
• CAS No.: 80014-87-5
• Molecular Formula: C19H23ClN2O5
• Molecular Weight: 394.84900
• DSSTox Substance ID: DTXSID90544423
• Wikidata: Q82421520
• Mol file: 80014-87-5.mol

Synonyms:80014-87-5;Diethyl N-{2-chloro-4-[(prop-2-yn-1-yl)amino]benzoyl}-L-glutamate;L-Glutamic acid, N-[2-chloro-4-(2-propynylamino)benzoyl]-, diethyl ester;SCHEMBL9556311;DTXSID90544423;diethyl (2S)-2-[[2-chloro-4-(prop-2-ynylamino)benzoyl]amino]pentanedioate

Chemical Property of Diethyl N-{2-chloro-4-[(prop-2-yn-1-yl)amino]benzoyl}-L-glutamate

Chemical Property:

• PSA: 97.22000
• LogP: 3.03770
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 394.1295495
• Heavy Atom Count: 27
• Complexity: 560

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCC(C(=O)OCC)NC(=O)C1=C(C=C(C=C1)NCC#C)Cl
• Isomeric SMILES: CCOC(=O)CC[C@@H](C(=O)OCC)NC(=O)C1=C(C=C(C=C1)NCC#C)Cl

Technology Process of Diethyl N-{2-chloro-4-[(prop-2-yn-1-yl)amino]benzoyl}-L-glutamate

There total 4 articles about Diethyl N-{2-chloro-4-[(prop-2-yn-1-yl)amino]benzoyl}-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: 63.0%

diethyl N-(4-amino-2-chlorobenzoyl)-L-glutamate (80014-92-2) + propargyl bromide (106-96-7) → diethyl N-<2-chloro-4-(prop-2-ynylamino)benzoyl>-L-glutamate (80014-87-5)

Guidance literature:

With 2,6-dimethylpyridine; In N,N-dimethyl acetamide; for 16h; Ambient temperature;

DOI:10.1021/jm00154a007

Reference yield:

2-chloro-4-nitrobenzoic acid (99-60-5) → diethyl N-<2-chloro-4-(prop-2-ynylamino)benzoyl>-L-glutamate (80014-87-5)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂ / Heating

2: 72 percent / pyridine / toluene / 1.5 h / 0 - 25 °C

3: 44 percent / NaHCO₃, sodium dithionite / ethanol; H₂O / 1 h / Ambient temperature

4: 63 percent / 2,6-lutidine / N,N-dimethyl-acetamide / 16 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; thionyl chloride; sodium dithionite; sodium hydrogencarbonate; In ethanol; N,N-dimethyl acetamide; water; toluene;

DOI:10.1021/jm00154a007

Reference yield:

diethyl N-(2-chloro-4-nitrobenzoyl)-L-glutamate (80014-91-1) → diethyl N-<2-chloro-4-(prop-2-ynylamino)benzoyl>-L-glutamate (80014-87-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / NaHCO₃, sodium dithionite / ethanol; H₂O / 1 h / Ambient temperature

2: 63 percent / 2,6-lutidine / N,N-dimethyl-acetamide / 16 h / Ambient temperature

With 2,6-dimethylpyridine; sodium dithionite; sodium hydrogencarbonate; In ethanol; N,N-dimethyl acetamide; water;

DOI:10.1021/jm00154a007

upstream raw materials:

diethyl N-(4-amino-2-chlorobenzoyl)-L-glutamate

propargyl bromide

2-chloro-4-nitrobenzoic acid

diethyl N-(2-chloro-4-nitrobenzoyl)-L-glutamate

Downstream raw materials:

diethyl N-<2-chloro-4-prop-2-ynylamino>benzoyl>-L-glutamate

(S)-2-{2-Chloro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid diethyl ester

N-<2-chloro-4-prop-2-ynylamino>benzoyl>-L-glutamic acid

(S)-2-{2-Chloro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid