(1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Base Information

• Chemical Name: (1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
• CAS No.: 1256387-76-4
• Molecular Formula: C₄₂H₄₈N₆O₄
• Molecular Weight: 700.881
• Mol file: 1256387-76-4.mol

Synonyms:(1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Chemical Property of (1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

There total 14 articles about (1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate 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: 45.0%

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester (1256387-74-2) + C30H38BN3O4 (1273592-38-3) → (1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (1256387-76-4)

Guidance literature:

With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; at 98 ℃; for 2.5h; Inert atmosphere;

Reference yield: 40.0%

(S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (1007882-04-3) + (1R,3S,4S)-tert-butyl 3-(6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (1256387-75-3) → (1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (1256387-76-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; water; at 90 ℃; Inert atmosphere;

DOI:10.1021/jm401499g

Reference yield:

(S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (1007882-12-3) → (1R,3S,4S)-tert-butyl 3-(6-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Himidazol-5-yl)biphenyl-4-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (1256387-76-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydrogencarbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 95 - 99 °C / Inert atmosphere

2: potassium acetate / bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 1.5 h / 90 °C / Inert atmosphere

3: sodium hydrogencarbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 2.5 h / 98 °C / Inert atmosphere

With potassium acetate; sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; dimethyl sulfoxide;

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

(S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

(S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

tert-butyl (2S)-2-[5-(4'-bromobiphenyl-4-yl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate

Downstream raw materials:

methyl (S)-1-((S)-2-(5-(4'-(2-((1R,3S,4S)-2-((S)-2-(acetoxyamino)-3-methylbutanoyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-benzo[d]imidazol-6-yl)biphenyl-4-yl)-1Himidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate