2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

Base Information

• Chemical Name: 2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid
• CAS No.: 1477523-87-7
• Molecular Formula: C₂₇H₂₉N₃O₄
• Molecular Weight: 459.545
• Mol file: 1477523-87-7.mol

Synonyms:2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

Chemical Property of 2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

There total 9 articles about 2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid 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: 92.0%

methyl 2-(4-(4'-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-28-9) → 2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid (1477523-87-7)

Guidance literature:

With methanol; sodium hydroxide; In tetrahydrofuran; at 20 ℃;

Reference yield:

methyl 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate (1477524-04-1) → 2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid (1477523-87-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

2.1: toluene-4-sulfonic acid / water; acetone / 1 h / 75 °C

3.1: sodium hydride / mineral oil; methanol / 0.5 h / 20 °C

3.2: 18 h / 20 °C

4.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / 20 - 100 °C / Cooling with ice

5.1: bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); cesium fluoride / 1,4-dioxane; water / 90 °C / Inert atmosphere

6.1: lithium hydroxide; water / methanol; tetrahydrofuran / 5 h / 40 °C

With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); water; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; cesium fluoride; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetone; toluene; mineral oil; 3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination / 4.1: |Michael Addition;

DOI:10.1021/acsmedchemlett.9b00117

Reference yield:

(8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol (1477524-05-2) → 2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid (1477523-87-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / water; acetone / 1 h / 75 °C

2.1: sodium hydride / mineral oil; methanol / 0.5 h / 20 °C

2.2: 18 h / 20 °C

3.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / 20 - 100 °C / Cooling with ice

4.1: bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); cesium fluoride / 1,4-dioxane; water / 90 °C / Inert atmosphere

5.1: lithium hydroxide; water / methanol; tetrahydrofuran / 5 h / 40 °C

With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); water; sodium hydride; toluene-4-sulfonic acid; cesium fluoride; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetone; mineral oil; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination / 3.1: |Michael Addition;

DOI:10.1021/acsmedchemlett.9b00117

upstream raw materials:

methyl 2-(4-(4'-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

methyl 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate

(8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol

(4-bromo-phenyl)-acetic acid methyl ester