(R)-methyl 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)pent-4-ynoate

Base Information

• Chemical Name: (R)-methyl 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)pent-4-ynoate
• CAS No.: 1266401-02-8
• Molecular Formula: C₂₆H₂₁F₃O₃
• Molecular Weight: 438.446
• Mol file: 1266401-02-8.mol

Synonyms:(R)-methyl 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)pent-4-ynoate

Chemical Property of (R)-methyl 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)pent-4-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-methyl 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)pent-4-ynoate

There total 14 articles about (R)-methyl 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)pent-4-ynoate 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%

C29H29F3O3Si → (R)-methyl 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)pent-4-ynoate (1266401-02-8)

Guidance literature:

With ammonium fluoride; In methanol; at 20 ℃; for 36h; enantioselective reaction;

DOI:10.1021/jacs.0c05373

Reference yield:

3-(4-hydroxyphenyl)propionic acid methyl ester (5597-50-2) → (R)-methyl 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)pent-4-ynoate (1266401-02-8)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetonitrile / 6 h / Reflux

2: diethylacetamide; (3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole); copper(l) iodide; sodium carbonate; 1,2,4,5-Tetrafluorobenzene; N-fluorobis(benzenesulfon)imide / 108 h / 5 °C / Inert atmosphere; Sealed tube; Schlenk technique

3: ammonium fluoride / methanol / 36 h / 20 °C

With ammonium fluoride; copper(l) iodide; diethylacetamide; 1,2,4,5-Tetrafluorobenzene; (3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole); sodium carbonate; potassium carbonate; N-fluorobis(benzenesulfon)imide; In methanol; acetonitrile;

DOI:10.1021/jacs.0c05373

Reference yield:

3-(bromomethyl)-4'-(trifluoromethyl)-1,1'-biphenyl (638214-11-6) + C12H12O3 (1266401-01-7) → (R)-methyl 3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)pent-4-ynoate (1266401-02-8)

Guidance literature:

With caesium carbonate; cesium iodide; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/ol102998w

upstream raw materials:

3-(bromomethyl)-4'-(trifluoromethyl)-1,1'-biphenyl

C₁₂H₁₂O₃

(E)-4-(3-(dimethylamino)-3-oxoprop-1-en-1-yl)phenyl acetate

(E)-4-(3-(dimethylamino)-3-thioxoprop-1-en-1-yl)phenyl acetate

Downstream raw materials:

[3H]-AMG 837

(3S)-3-[4-(4'-trifluoromethyl-biphenyl-3-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester