2-methoxy-N-[(1R)-1-phenylethyl]acetamide

Base Information

• Chemical Name: 2-methoxy-N-[(1R)-1-phenylethyl]acetamide
• CAS No.: 162929-44-4
• Molecular Formula: C11H15NO2
• Molecular Weight: 193.246
• European Community (EC) Number: 605-310-5
• DSSTox Substance ID: DTXSID50356847
• Nikkaji Number: J1.374.984A
• Wikidata: Q82136453
• Mol file: 162929-44-4.mol

Synonyms:2-MET cpd;2-methoxy-N-((1R)-1-phenylethyl)acetamide;2-methoxy-N-(1-phenylethyl)acetamide

Chemical Property of 2-methoxy-N-[(1R)-1-phenylethyl]acetamide

Chemical Property:

• Vapor Pressure: 4.3E-05mmHg at 25°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 176

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)NC(=O)COC
• Isomeric SMILES: C[C@H](C1=CC=CC=C1)NC(=O)COC

Technology Process of 2-methoxy-N-[(1R)-1-phenylethyl]acetamide

There total 22 articles about 2-methoxy-N-[(1R)-1-phenylethyl]acetamide 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: 100.0%

ethyl 2-methoxyacetate (3938-96-3) + rac-methylbenzylamine (618-36-0) → (R)-2-methoxy-N-(1-phenylethyl)acetamide (162929-44-4)

Guidance literature:

With Candida antartica lipase B; hydrogen; In toluene; at 70 ℃; for 6h; under 760.051 Torr; Temperature; Reagent/catalyst; Time; Molecular sieve;

DOI:10.1021/jo500508p

Reference yield: 92.0%

isopropyl methoxyacetate (17640-21-0) + rac-methylbenzylamine (618-36-0) → (R)-2-methoxy-N-(1-phenylethyl)acetamide (162929-44-4)

Guidance literature:

With sodium carbonate; In toluene; at 70 ℃; for 6h; optical yield given as %ee; Inert atmosphere; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetlet.2010.08.050

Reference yield: 88.0%

2-methoxy-ethanol (109-86-4,95507-80-5) + (R)-1-phenyl-ethyl-amine (3886-69-9) → (R)-2-methoxy-N-(1-phenylethyl)acetamide (162929-44-4)

Guidance literature:

With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium hydroxide; In toluene; at 110 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tet.2014.03.085

upstream raw materials:

ethyl 2-methoxyacetate

rac-methylbenzylamine

isopropyl methoxyacetate

acetophenone oxime

Downstream raw materials:

(R)-N-(2-methoxyethyl)(1-phenylethyl)amine

(R)-1-phenyl-ethyl-amine

2-methoxyacetic acid

methoxyacetic acid sodium salt

Refernces

• 1、 Oláh, Márk,Boros, Zoltán,Hornyánszky, Gábor,Poppe, László. "Isopropyl 2-ethoxyacetate—an efficient acylating agent for lipase-catalyzed kinetic resolution of amines in batch and continuous-flow modes". . p. 7249 - 7255. Retrieved 2016.
• 2、 De Miranda, Amanda S.,De Souza, Rodrigo O. M. A.,Miranda, Leandro S. M.. "Ammonium formate as a green hydrogen source for clean semi-continuous enzymatic dynamic kinetic resolution of (+/-)-α-methylbenzylamine". . p. 13620 - 13625. Retrieved 2014.
• 3、 Balkenhohl, Friedhelm,Ditrich, Klaus,Hauer, Bernhard,Ladner, Wolfgang. "Optically active amines via lipase-catalyzed methoxyacetylation". . p. 381 - 384. Retrieved 1997.
• 4、 Engstroem, Karin,Johnston, Eric V.,Verho, Oscar,Gustafson, Karl P. J.,Shakeri, Mozaffar,Tai, Cheuk-Wai,Baeckvall, Jan-E.. "Co-immobilization of an enzyme and a metal into the compartments of mesoporous silica for cooperative tandem catalysis: An artificial metalloenzyme". . p. 14006 - 14010. Retrieved 2013.
• 5、 de Souza, Stefania P.,Le?o, Raquel A.C.,Bassut, Jonathan F.,Leal, Ivana C.R.,Wang, Shuai,Ding, Qiqi,Li, Yingying,Lam, Frank Leung-Yuk,de Souza, Rodrigo O.M.A.,Itabaiana Jr, Ivaldo. "New Biosilified Pd-lipase hybrid biocatalysts for dynamic resolution of amines". . p. 4849 - 4854. Retrieved 2017.
• 6、 B?ckvall, Jan-E.,Córdova, Armando,Deiana, Luca,Naidu, Veluru Ramesh,Rafi, Abdolrahim A.,Tai, Cheuk-Wai. "Artificial plant cell walls as multi-catalyst systems for enzymatic cooperative asymmetric catalysis in non-aqueous media". supporting information. p. 8814 - 8817. Retrieved 2021/09/07.
• 7、 Gao, Liya,Wang, Zihan,Liu, Yunting,Liu, Pengbo,Gao, Shiqi,Gao, Jing,Jiang, Yanjun. "Co-immobilization of metal and enzyme into hydrophobic nanopores for highly improved chemoenzymatic asymmetric synthesis". supporting information. p. 13547 - 13550. Retrieved 2020/11/17.