(S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester

Base Information

Chemical Name:(S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester
CAS No.:496790-54-6
Molecular Formula:C₂₅H₂₅BrN₂O₂
Molecular Weight:465.39
Hs Code.:

Synonyms:(S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester

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Chemical Property of (S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester

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Technology Process of (S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester

There total 7 articles about (S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl 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: 77.0%

: 81477-94-3
N-(diphenylmethylene)glycine tert-butyl ester

: 94446-97-6
2-bromo-3-bromomethylpyridine

: 496790-54-6
(S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester

Guidance literature:: With cesium hydroxide; cinchonidinium bromide derived chiral; for 20h;
DOI:10.1021/ja0284308

Reference yield:

: 81477-94-3
N-(diphenylmethylene)glycine tert-butyl ester

: 94446-97-6
2-bromo-3-bromomethylpyridine

: 496790-55-7
(R)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester

: 496790-54-6
(S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester

Guidance literature:: N-(diphenylmethylene)glycine tert-butyl ester; 2-bromo-3-bromomethylpyridine; With cinchonidine derived compound; In dichloromethane; at -78 ℃; for 0.25h;

With cesium hydroxide; In dichloromethane; at -60 ℃; for 72h; Title compound not separated from byproducts;
DOI:10.1055/s-2004-831226

Reference yield:

: 109-04-6
2-bromo-pyridine

: 496790-54-6
(S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi; (i-Pr)2NH / tetrahydrofuran; hexane / 1.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 4 h / -78 °C

2.1: 11.3 g / NaBH₄ / methanol / 12 h

3.1: 88 percent / PBr₃ / CH₂Cl₂ / 12 h / 20 °C

4.1: cinchonidine derived compound / CH₂Cl₂ / 0.25 h / -78 °C

4.2: CsOH*H₂O / CH₂Cl₂ / 72 h / -60 °C

With sodium tetrahydroborate; n-butyllithium; cinchonidine derived compound; phosphorus tribromide; diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1055/s-2004-831226