tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate
• CAS No.: 1287206-09-0
• Molecular Formula: C₂₃H₄₂N₂O₃Si
• Molecular Weight: 422.684
• Mol file: 1287206-09-0.mol

Synonyms:tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate

Chemical Property of tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate

There total 2 articles about tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate 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:

N-(t-butoxycarbonyl)-isoleucine aldehyde (118171-79-2,141321-51-9,141321-54-2,87694-55-1) + 4-[(tert-butyldimethylsilyl)oxy]aniline (111359-74-1) → tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate (1287206-09-0)

Guidance literature:

N-(t-butoxycarbonyl)-isoleucine aldehyde; 4-[(tert-butyldimethylsilyl)oxy]aniline; With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃;

With sodium hydrogencarbonate; In 1,2-dichloro-ethane;

Reference yield:

N-(tert-butoxycarbonyl)-L-isoleucinol (141321-52-0,141321-53-1,141321-50-8,106946-74-1,545433-88-3) → tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate (1287206-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0 °C

2: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C

With sulfur trioxide pyridine complex; sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane;

Reference yield: 83.0%

tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate (1287206-09-0) + trans-2-(5-fluoropyridin-2yl)cyclopropanecarboxylic acid hydrochloride → [(1S,2S)-1-({[4-(tert-butyldimethylsilanyloxy)phenyl][trans-2-(5-fluoropyridin-2-yl)cyclopropanecarbonyl]amino}methyl)-2-methylbutyl]carbamic acid tert-butyl ester (1287205-99-5)

Guidance literature:

trans-2-(5-fluoropyridin-2yl)cyclopropanecarboxylic acid hydrochloride; With thionyl chloride; Reflux;

tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate; With triethylamine; In dichloromethane; at 20 ℃;

upstream raw materials:

N-(tert-butoxycarbonyl)-L-isoleucinol

N-(t-butoxycarbonyl)-isoleucine aldehyde

4-[(tert-butyldimethylsilyl)oxy]aniline

Downstream raw materials:

tert-butyl (2S,3S)-1-(N-(4-(tert-butyldimethylsilyloxy)phenyl)-trans-2-(pyridin-2-yl)cyclopropanecarboxamido)-3-methylpentan-2-ylcarbamate

[(1S,2S)-1-({[4-(tert-butyldimethylsilanyloxy)phenyl][trans-2-(5-fluoropyridin-2-yl)cyclopropanecarbonyl]amino}methyl)-2-methylbutyl]carbamic acid tert-butyl ester

tert-butyl (2S,3S)-1-((1R,2R)-N-(4-hydroxyphenyl)-2-(pyridin-2-yl)cyclopropanecarboxamido)-3-methylpentan-2-ylcarbamate

(1R,2R)-2-pyridin-2-ylcyclopropanecarboxylic acid ((2S,3S)-2-amino-3-methylpentyl)-(4-(cyclobutylmethoxy)phenyl)amide