(S)-tert-butyl 2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate

Base Information

• Chemical Name: (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate
• CAS No.: 119244-29-0
• Molecular Formula: C₃₀H₂₉NO₂
• Molecular Weight: 435.566
• Mol file: 119244-29-0.mol

Synonyms:(S)-tert-butyl 2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate

Chemical Property of (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate

There total 4 articles about (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate 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: 97.0%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + 2-bromomethylnaphthyl bromide (939-26-4) → (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate (119244-29-0)

Guidance literature:

With sodium hydroxide; trimeric cinchona alkaloid; In dichloromethane; toluene; at -10 ℃; for 7h;

DOI:10.1055/s-2005-872170

Reference yield:

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + 2-bromomethylnaphthyl bromide (939-26-4) → tert-butyl (R)-2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate + (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate (119244-29-0)

Guidance literature:

With potassium hydroxide; N-anthracenyl methyl cinchonidium chloride; In water; toluene; for 18h; Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1016/S0040-4039(97)10293-3

Reference yield:

Benzophenone imine (1013-88-3) → tert-butyl (R)-2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate + (S)-tert-butyl 2-(diphenylmethyleneamino)-3-(naphthalen-2-yl)propanoate (119244-29-0)

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

2-bromomethylnaphthyl bromide

Benzophenone imine

glycine tert-butyl ester hydrochloride

Refernces

• 1、 Huynh, Florence,Tailby, Matthew,Finniear, Aled,Stephens, Kevin,Allemann, Rudolf K.,Wirth, Thomas. "Accelerating Biphasic Biocatalysis through New Process Windows". supporting information. p. 16490 - 16495. Retrieved 2020/07/17.
• 2、 Peng, Wenwen,Wan, Jingwei,Xie, Bing,Ma, Xuebing. "9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts". . p. 8336 - 8345. Retrieved 2015/01/08.