(+/-)-N-(BENZYLIDENE)ALANINE ETHYL ESTER

Base Information

• Chemical Name: (+/-)-N-(BENZYLIDENE)ALANINE ETHYL ESTER
• CAS No.: 60930-36-1
• Molecular Formula: C12H15NO2
• Molecular Weight: 205.257
• Mol file: 60930-36-1.mol

Synonyms:(+/-)-N-(BENZYLIDENE)ALANINE ETHYL ESTER;2-(BenzylideneaMino)propionic Acid Ethyl Ester;N-(PhenylMethylene)alanine Ethyl Ester;Ethyl N-Benzylidenealaninate

Chemical Property of (+/-)-N-(BENZYLIDENE)ALANINE ETHYL ESTER

Chemical Property:

• PSA: 38.66000
• LogP: 2.05710
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

(+/-)-N-(Benzylidene)alanineEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+/-)-N-(BENZYLIDENE)ALANINE ETHYL ESTER

There total 2 articles about (+/-)-N-(BENZYLIDENE)ALANINE ETHYL 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: 92.2%

DL-alanine ethyl ester hydrochloride (617-27-6) + benzaldehyde (100-52-7) → ethyl (RS)-2-(benzylideneamino)propanoate (60930-36-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 25 ℃; for 5h; Product distribution / selectivity;

Reference yield:

ethyl 2-aminopropanoate hydrochloride + benzaldehyde (100-52-7) → ethyl (RS)-2-(benzylideneamino)propanoate (60930-36-1)

Guidance literature:

ethyl 2-aminopropanoate hydrochloride; With magnesium sulfate; triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

benzaldehyde; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1039/d0cc01061h

Reference yield: 100.0%

tert-Butyl acrylate (1663-39-4,25232-27-3) + ethyl (RS)-2-(benzylideneamino)propanoate (60930-36-1) → 4-tert-butyl 2-ethyl 2-methyl-5-phenylpyrrolidine-2,4-dicarboxylate

Guidance literature:

With calcium bis-iso-propoxide; (S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline); In tetrahydrofuran; at 10 ℃; for 3h; optical yield given as %ee; enantioselective reaction; Molecular sieve;

DOI:10.1021/ja8032058

upstream raw materials:

DL-alanine ethyl ester hydrochloride

benzaldehyde

Downstream raw materials:

2-Methyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-hexanoic acid ethyl ester

N-benzylalanine ethyl ester

2-amino-3-hydroxy-2-methyl-propionic acid

ethyl 2-(hydroxymethyl)-2-aminopropionate

Refernces

• 1、 Korch, Katerina M.,Eidamshaus, Christian,Behenna, Douglas C.,Stoltz, Brian M.,Nam, Sangkil,Horne, David. "Enantioselective synthesis of α-secondary and α-tertiary piperazin-2- Ones and piperazines by catalytic asymmetric allylic alkylation". supporting information. p. 179 - 183. Retrieved 2015/02/05.
• 2、 De Wachter, Rien,Brans, Luc,Ballet, Steven,Van den Eynde, Isabelle,Feytens, Debby,Keresztes, Attila,Toth, Geza,Urbanczyk-Lipkowska, Zofia,Tourwé, Dirk. "Influence of ring substitution on the conformation and β-turn mimicry of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one peptide mimetics". experimental part. p. 2266 - 2278. Retrieved 2009/08/08.