(S)-3-(4-((4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-ynoic acid

Base Information

• Chemical Name: (S)-3-(4-((4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-ynoic acid
• CAS No.: 865231-46-5
• Molecular Formula: C₂₆H₂₁F₃O₃
• Molecular Weight: 438.446
• Mol file: 865231-46-5.mol

Synonyms:(S)-3-(4-((4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-ynoic acid;AMG 837;(S)-3-(4-((4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-ynoic acid (AMG-837 free acid) 1259389-38-2 (calium salt hydrate);(betaS)-beta-1-Propyn-1-yl-4-[[4'-(trifluoromethyl)[1,1'-biphenyl]-3-yl]methoxy]benzenepropanoic acid

Chemical Property of (S)-3-(4-((4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-ynoic acid

Chemical Property:

• Melting Point: 139-142 °C
• Boiling Point: 565.8±50.0 °C(Predicted)
• PKA: 4.20±0.10(Predicted)
• PSA: 46.53000
• Density: 1.251±0.06 g/cm3(Predicted)
• LogP: 6.53300

Purity/Quality:

97% ^*data from raw suppliers

AMG837 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: AMG 837 is a potent GPR40 agonist. GPR40 is a polyunsaturated fatty acid receptor that is involved with many systemic effects, which are beneficial for metabolic and inflammatory diseases. GPR40 has also been implicated as a target for treating obesity.

Technology Process of (S)-3-(4-((4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-ynoic acid

There total 63 articles about (S)-3-(4-((4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-ynoic 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: 100.0%

(3S)-3-[4-(4'-trifluoromethyl-biphenyl-3-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (865233-37-0) → [3H]-AMG 837 (865231-46-5)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 20 ℃; for 16h;

DOI:10.1021/ol102998w

Reference yield: 92.0%

ethyl (S)-3-(4-((4'-(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)hex-4-ynoate → [3H]-AMG 837 (865231-46-5)

Guidance literature:

With ethanol; sodium hydroxide; at 20 ℃; for 5h;

Reference yield: 89.0%

3-(bromomethyl)-4'-(trifluoromethyl)-1,1'-biphenyl (638214-11-6) + (3S)-3-(4-hydroxy-phenyl)-hex-4-ynoic acid (865233-35-8) → [3H]-AMG 837 (865231-46-5)

Guidance literature:

With tetra-n-butylphosphonium hydroxide; In tetrahydrofuran; water; at -5 - 20 ℃; for 21h;

DOI:10.1021/op1003055

upstream raw materials:

(+/-)-5-[1-(4-hydroxy-phenyl)-but-2-ynyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione

4-hydroxy-β-1-propyn-1-ylbenzenepropanoic acid

(+/-)-ethyl 3-(4-((4-methoxybenzyl)oxy)phenyl)hex-4-ynoate

(+/-)-ethyl 3-(4-hydroxyphenyl)hex-4-ynoate