tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate

Base Information

• Chemical Name: tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate
• CAS No.: 1394857-67-0
• Molecular Formula: C₂₉H₄₁N₅O₆
• Molecular Weight: 555.674
• Mol file: 1394857-67-0.mol

Synonyms:tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate

Chemical Property of tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate

There total 9 articles about tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate 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: 10.0%

Nα-tert-butyloxycarbonyl-L-ornithine tert-butyl ester hydrochloride + C15H14IN3O2 (1394857-66-9) → tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate (1394857-67-0)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; Inert atmosphere; Reflux;

DOI:10.1021/ol3021226

Reference yield:

1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridine (1365094-40-1) → tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate (1394857-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / tert-butyl alcohol / 18 h / 120 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; tert-butyl alcohol;

DOI:10.1021/ol3021226

Reference yield:

2-chloro-N-(2,4-dimethoxybenzyl)pyridin-3-amine (1154721-78-4) → tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate (1394857-67-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate / tert-butyl alcohol / 5 h / 110 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / tert-butyl alcohol / 18 h / 120 °C / Inert atmosphere

With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium phosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; tert-butyl alcohol;

DOI:10.1021/ol3021226

upstream raw materials:

1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridine

Boc-Orn(Z)-OH

N_α-(1,1-dimethylethoxycarbonyl)-N_δ-(phenylmethoxycarbonyl)-L-ornithine 1,1-dimethylethyl ester

C₁₅H₁₄IN₃O₂

Downstream raw materials:

C₄₄H₆₉N₆O₁₀⁽¹⁺⁾*I^(1-)