N-(2-Ethyl-6-methylphenyl)-L-alanine

Base Information

• Chemical Name: N-(2-Ethyl-6-methylphenyl)-L-alanine
• CAS No.: 82508-03-0
• Molecular Formula: C12H17NO2
• Molecular Weight: 207.272
• European Community (EC) Number: 635-722-0
• DSSTox Substance ID: DTXSID90509799
• Nikkaji Number: J2.434.363D
• Wikidata: Q76422892
• Mol file: 82508-03-0.mol

Synonyms:82508-03-0;N-(2-Ethyl-6-methylphenyl)-L-alanine;(2S)-2-(2-ethyl-6-methylanilino)propanoic acid;L-Alanine, N-(2-ethyl-6-methylphenyl)-;N-(2-Ethyl-6-methylphenyl)alanine;S-Metolachlor Metabolite CGA 50267;Metolachlor CGA 50267;SCHEMBL9777510;DTXSID90509799;(2S)-2-[(2-ETHYL-6-METHYLPHENYL)AMINO]PROPANOIC ACID;CGA 50267;NS00067577;(S)-2-((2-Ethyl-6-methylphenyl)amino)propanoic acid;(S)-2-((2-Ethyl-6-methylphenyl)amino)propanoicacid;S-Metolachlor Metabolite CGA 50267, PESTANAL(R), analytical standard

Chemical Property of N-(2-Ethyl-6-methylphenyl)-L-alanine

Chemical Property:

• PSA: 49.33000
• LogP: 2.51540
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 207.125928785
• Heavy Atom Count: 15
• Complexity: 218

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=CC=CC(=C1NC(C)C(=O)O)C
• Isomeric SMILES: CCC1=CC=CC(=C1N[C@@H](C)C(=O)O)C
• Uses: N-(2-Ethyl-6-methylphenyl)-L-alanine is used in the chemoenzymic synthesis of the chiral herbicide (S)-metolachlor. A pesticide metabolite.

Technology Process of N-(2-Ethyl-6-methylphenyl)-L-alanine

There total 2 articles about N-(2-Ethyl-6-methylphenyl)-L-alanine 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:

N-(1'-methoxy-carbonyl-ethyl)-2-methyl-6-ethyl-aniline (69516-03-6,75386-37-7,57836-79-0) → (S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alanin (82508-03-0) + (R)-(+)-N-(2-Ethyl-6-methyl-phenyl)-alaninmethylester (75386-37-7)

Guidance literature:

With Candida antarctica lipase B; sodium hydroxide; phosphate buffer; In diethyl ether; water; at 25 ℃; pH=8.0;

DOI:10.1139/V06-129

Reference yield:

6-ethyl-o-toluidine (24549-06-2) → (S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alanin (82508-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 67.2 percent / NaHCO₃ / 19 h / 120 - 125 °C

2: 1.0 g / Candida antarctica lipase B; phosphate buffer; NaOH / H₂O; diethyl ether / 25 °C / pH 8.0

With Candida antarctica lipase B; sodium hydroxide; phosphate buffer; sodium hydrogencarbonate; In diethyl ether; water;

DOI:10.1139/V06-129

Reference yield:

chloroacetyl chloride (79-04-9) + 2,2-dimethoxy-propane (77-76-9) + (S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alanin (82508-03-0) → (aRS,1'R)-(+)-N-(1'-Methyl-2'-methoxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin (178961-20-1) + (S)-metolachlor (87392-12-9)

Guidance literature:

(S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alanin; With sodium tetrahydroborate; sulfuric acid; In tetrahydrofuran; at 20 ℃;

chloroacetyl chloride; With sodium carbonate; In benzene; at 20 ℃; for 3h;

2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In methanol; for 36h; Title compound not separated from byproducts; Heating;

DOI:10.1139/V06-129

upstream raw materials:

N-(1'-methoxy-carbonyl-ethyl)-2-methyl-6-ethyl-aniline

6-ethyl-o-toluidine

Downstream raw materials:

(S)-(-)-N-(2-Ethyl-6-methyl-phenyl)-alaninmethylester

(S)-(-)-N-(1'-Methyl-2'-hydroxyethyl)-2-ethyl-6-methylanilin

(aRS,1'R)-(+)-N-(1'-Methyl-2'-methoxyethyl)-N-chloracetyl-2-ethyl-6-methylanilin

(S)-metolachlor

Refernces

• 1、 Moser,Rihs,Sauter. "The influence of atropisomerism and chiral centre on the biological activity of metolachlor". . p. 451 - 462. Retrieved 2007/10/02.