{(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic acid tert-butyl ester
• CAS No.: 1329167-92-1
• Molecular Formula: C₂₅H₃₀N₄O₅
• Molecular Weight: 466.537
• Mol file: 1329167-92-1.mol

Synonyms:{(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic acid tert-butyl ester

Chemical Property of {(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic acid tert-butyl ester

There total 9 articles about {(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic 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: 88.0%

pent-4-enoic acid (591-80-0) + tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate (1329167-90-9) → {(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic acid tert-butyl ester (1329167-92-1)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; at -5 - 20 ℃;

Reference yield:

4-chloro-2-pyridinecarbaldehyde (63071-13-6) → {(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic acid tert-butyl ester (1329167-92-1)

Guidance literature:

Multi-step reaction with 6 steps

1: copper(II) sulfate / dichloromethane / 3 h / 20 °C

2: diethyl ether; tetrahydrofuran / -78 °C

3: potassium phosphate; water / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 5 h / 90 °C

4: hydrogenchloride / 1,4-dioxane; methanol

5: triethylamine / dichloromethane / 2 h / 20 °C

6: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / -5 - 20 °C

With hydrogenchloride; potassium phosphate; water; copper(II) sulfate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate;

Reference yield:

2-bromo 5-nitroaniline (10403-47-1) → {(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic acid tert-butyl ester (1329167-92-1)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 4 h / 80 °C / Inert atmosphere

2: potassium phosphate; water / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 5 h / 90 °C

3: hydrogenchloride / 1,4-dioxane; methanol

4: triethylamine / dichloromethane / 2 h / 20 °C

5: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / -5 - 20 °C

With hydrogenchloride; potassium phosphate; water; potassium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate;

upstream raw materials:

di-tert-butyl dicarbonate

pent-4-enoic acid

tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate

4-chloro-2-pyridinecarbaldehyde

Downstream raw materials:

C₂₅H₃₂N₄O₃

{4-[2-((S)-1-tert-butoxycarbonylaminobut-3-enyl)pyridin-4-yl]-3-pent-4-enoylaminophenyl}carbamic acid methyl ester