Ethyl 2-amino-2-phenylbutanoate

Base Information

• Chemical Name: Ethyl 2-amino-2-phenylbutanoate
• CAS No.: 6480-87-1
• Molecular Formula: C12H17NO2
• Molecular Weight: 207.26900
• DSSTox Substance ID: DTXSID10440736
• Nikkaji Number: J89.678K
• Mol file: 6480-87-1.mol

Synonyms:ethyl 2-amino-2-phenylbutanoate;2-Ethyl-2-phenylglycine Ethyl Ester;6480-87-1;SCHEMBL1455681;DTXSID10440736;JLEZVTIYNCKTNH-UHFFFAOYSA-N;2-amino-2-phenylbutyric acid ethyl ester;FT-0668369;EN300-4239603;(+)-alpha-Amino-alpha-ethylbenzeneacetic acid ethyl ester;52165-63-6

Chemical Property of Ethyl 2-amino-2-phenylbutanoate

Chemical Property:

• PSA: 52.32000
• LogP: 2.51400
• Solubility.: Dichloromethane
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 207.125928785
• Heavy Atom Count: 15
• Complexity: 212

Purity/Quality:

97% ^*data from raw suppliers

2-Ethyl-2-phenylglycineEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1=CC=CC=C1)(C(=O)OCC)N
• Uses: Intermediate in the preparation of Trimebutine metabolites.

Technology Process of Ethyl 2-amino-2-phenylbutanoate

There total 9 articles about Ethyl 2-amino-2-phenylbutanoate 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: 95.0%

ethyl 2-amino-2-phenylbutanoate hydrochloride (27856-08-2) → ethyl 2-amino-2-phenylbutanoate (6480-87-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 0.333333h;

Reference yield: 64.0%

ethyl (Z)-2-phenyl-2-[(trimethylsilyl)imino]acetate + diethylaluminium chloride (96-10-6) → ethyl 2-amino-2-phenylbutanoate (6480-87-1) + ethyl 2-(ethylamino)-2-phenylacetate (37563-27-2)

Guidance literature:

In 1,4-dioxane; hexane; at 20 ℃; for 3h; Solvent;

DOI:10.1021/acs.orglett.9b00654

Reference yield: 17.0%

ethyl (Z)-2-phenyl-2-[(trimethylsilyl)imino]acetate + diethylaluminium chloride (96-10-6) → ethyl 2-amino-2-phenylbutanoate (6480-87-1)

Guidance literature:

In hexane; 1,2-dichloro-ethane; at 20 ℃; for 3h; Solvent;

DOI:10.1021/acs.orglett.9b00654

upstream raw materials:

ethyl 2-amino-2-phenylbutanoate hydrochloride

phenylglycine ethyl ester hydrochloride

ethyl N-(phenylmethylene)glycinate

phenylglycin

Downstream raw materials:

2-(N-formyl)-methylamino-2-phenylbutanol

2-methylamino-2-phenylbutanol

Nortrimebutine

2-formylamino-2-phenyl-butyric acid ethyl ester

Refernces

• 1、 Martin, Arnaud,Figadere, Bruno,Saivin, Sylvie,Houin, Georges,Chomard, Jean Marie,Cahiez, Gerard. "Synthesis of methylamino-2-phenyl-2-butyl-3,4,5-trimethoxybenzoate, the main bioactive metabolite of trimebutine maleate". . p. 544 - 549. Retrieved 2007/10/03.