(R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate

Base Information

• Chemical Name: (R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate
• CAS No.: 1579514-19-4
• Molecular Formula: C₂₇H₂₆F₃N₃O₅S
• Molecular Weight: 561.582
• Mol file: 1579514-19-4.mol

Synonyms:(R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate

Chemical Property of (R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate

There total 5 articles about (R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate 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: 35.0%

trifluoromethylsulfonic anhydride (358-23-6) + (R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one (1579513-50-0) → (R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate (1579514-19-4)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 2h;

Reference yield:

(R)-5-(4-bromophenyl)-6-((1-(cyclopropanecarbonyl) pyrrolidin-3-yl)methyl)-4,6-diazaspiro[2.4]hept-4-en-7-one (1579512-01-8) → (R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate (1579514-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 3 h / Inert atmosphere; Reflux

2: pyridine / dichloromethane / 2 h / 0 - 20 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; dichloromethane; water;

Reference yield:

4-Bromobenzoic acid (586-76-5) → (R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate (1579514-19-4)

Guidance literature:

Multi-step reaction with 5 steps

1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C

2: 48 h / Heating

3: caesium carbonate / N,N-dimethyl-formamide / 6 h / 65 °C

4: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 3 h / Inert atmosphere; Reflux

5: pyridine / dichloromethane / 2 h / 0 - 20 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2018.05.014

upstream raw materials:

trifluoromethylsulfonic anhydride

(R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one

(R)-5-(4-bromophenyl)-6-((1-(cyclopropanecarbonyl) pyrrolidin-3-yl)methyl)-4,6-diazaspiro[2.4]hept-4-en-7-one

4-Bromobenzoic acid

Downstream raw materials:

(R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-(1-methyl-1H-pyrazol-4-yl)-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one