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

Base Information

• Chemical Name: tert-butyl (2S,3S)-1-(N-(4-(tert-butyldimethylsilyloxy)phenyl)-trans-2-(pyridin-2-yl)cyclopropanecarboxamido)-3-methylpentan-2-ylcarbamate
• CAS No.: 1287206-02-3
• Molecular Formula: C₃₂H₄₉N₃O₄Si
• Molecular Weight: 567.844
• Mol file: 1287206-02-3.mol

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

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

There total 3 articles about tert-butyl (2S,3S)-1-(N-(4-(tert-butyldimethylsilyloxy)phenyl)-trans-2-(pyridin-2-yl)cyclopropanecarboxamido)-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: 77.0%

(1,2-trans)-2-pyridin-2'-yl-cyclopropanecarboxylic acid + tert-butyl (2S,3S)-1-(4-(tert-butyldimethylsilyloxy)phenylamino)-3-methylpentan-2-ylcarbamate (1287206-09-0) → tert-butyl (2S,3S)-1-(N-(4-(tert-butyldimethylsilyloxy)phenyl)-trans-2-(pyridin-2-yl)cyclopropanecarboxamido)-3-methylpentan-2-ylcarbamate (1287206-02-3)

Guidance literature:

(1,2-trans)-2-pyridin-2'-yl-cyclopropanecarboxylic acid; With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 35 ℃; for 3h;

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

Reference yield:

N-(t-butoxycarbonyl)-isoleucine aldehyde (118171-79-2,141321-51-9,141321-54-2,87694-55-1) → tert-butyl (2S,3S)-1-(N-(4-(tert-butyldimethylsilyloxy)phenyl)-trans-2-(pyridin-2-yl)cyclopropanecarboxamido)-3-methylpentan-2-ylcarbamate (1287206-02-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 3 h / 35 °C

2.2: 20 °C

With oxalyl dichloride; sodium tris(acetoxy)borohydride; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

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-(N-(4-(tert-butyldimethylsilyloxy)phenyl)-trans-2-(pyridin-2-yl)cyclopropanecarboxamido)-3-methylpentan-2-ylcarbamate (1287206-02-3)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 3 h / 35 °C

3.2: 20 °C

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

upstream raw materials:

N-(tert-butoxycarbonyl)-L-isoleucinol

N-(t-butoxycarbonyl)-isoleucine aldehyde

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

Downstream raw materials:

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