Butanoic acid, 4-cyano-2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2S)-

Base Information

• Chemical Name: Butanoic acid, 4-cyano-2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2S)-
• CAS No.: 271601-28-6
• Molecular Formula: C22H24N2O2
• Molecular Weight: 348.445
• Mol file: 271601-28-6.mol

Synonyms:

Chemical Property of Butanoic acid, 4-cyano-2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Butanoic acid, 4-cyano-2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2S)-

There total 4 articles about Butanoic acid, 4-cyano-2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2S)- 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: 90.0%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + acrylonitrile (107-13-1,25014-41-9) → 1,1-dimethylethyl 4-cyano-(2S)-[(diphenylmethylene)amino]butanoate (271601-28-6) + 1,1-dimethylethyl 4-cyano-(2R)-[(diphenylmethylene)amino]butanoate

Guidance literature:

With C₃₄H₅₀CoN₄O₂⁽¹⁺⁾*Cl^(1-); potassium hydroxide; In dichloromethane; water; at 0 ℃; for 2h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201400091

Reference yield:

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + acrylonitrile (107-13-1,25014-41-9) → 1,1-dimethylethyl 4-cyano-(2S)-[(diphenylmethylene)amino]butanoate (271601-28-6)

Guidance literature:

With potassium hydroxide; N-(9-antracenylmethyl)cinchonidinium bromide; In dichloromethane; at -55 ℃; for 15h;

DOI:10.1021/ol0056527

Reference yield:

Benzophenone imine (1013-88-3) → 1,1-dimethylethyl 4-cyano-(2S)-[(diphenylmethylene)amino]butanoate (271601-28-6) + 1,1-dimethylethyl 4-cyano-(2R)-[(diphenylmethylene)amino]butanoate

Guidance literature:

Multi-step reaction with 2 steps

1: 3 h / 20 °C / neat (no solvent)

2: O-⁽⁹⁾-allyl-N-(anthracene-9-yl)methylcinchonidinium bromide; potassium hydroxide / 1 h / 20 °C / neat (no solvent)

With O-⁽⁹⁾-allyl-N-(anthracene-9-yl)methylcinchonidinium bromide; potassium hydroxide;

DOI:10.1002/chem.201102885

upstream raw materials:

N-(diphenylmethylene)glycine tert-butyl ester

acrylonitrile

Benzophenone imine

glycine tert-butyl ester hydrochloride

Downstream raw materials:

dihydrochloride of (S)-ornithine

5-amino-2-(benzhydryl-amino)-pentanoic acid tert-butyl ester

L-ornithine hydrochloride

Refernces

• 1、 Bandar, Jeffrey S.,Barthelme, Alexandre,Mazori, Alon Y.,Lambert, Tristan H.. "Structure-activity relationship studies of cyclopropenimines as enantioselective Bronsted base catalysts". . p. 1537 - 1547. Retrieved 2015/02/05.
• 2、 -. "CYCLOPROPENIMINE CATALYST COMPOSITIONS AND PROCESSES". Paragraph 0208; 0221. . Retrieved 2013/05/09.