2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic acid

Base Information

• Chemical Name: 2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic acid
• CAS No.: 919361-00-5
• Molecular Formula: C₂₁H₂₂N₂O₄
• Molecular Weight: 366.417
• Mol file: 919361-00-5.mol

Synonyms:2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic acid

Chemical Property of 2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic acid

There total 8 articles about 2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic 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:

2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic acid ethyl ester → 2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic acid (919361-00-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 16h;

DOI:10.1016/j.bmcl.2006.08.110

Reference yield:

5-formyl-2-[2-(5-methyl-2-phenyl-4-oxazolyl)-ethoxy]pyridine (157169-61-4) → 2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic acid (919361-00-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / NaBH₄ / methanol / 1 h / 20 °C

2: 100 percent / (COCl)2 / dimethylformamide; CH₂Cl₂ / 3 h / 20 °C

3: 75 percent / NaI / acetone / 4 h / 20 °C

4: NaHMDS / tetrahydrofuran / 3 h / -50 °C

5: LiOH / tetrahydrofuran; methanol; H₂O / 16 h / 20 °C

With lithium hydroxide; sodium tetrahydroborate; oxalyl dichloride; sodium hexamethyldisilazane; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 3: Finkelstein reaction;

DOI:10.1016/j.bmcl.2006.08.110

Reference yield:

5-bromo-2-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridine (784149-29-7) → 2-methyl-3-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-yl}-propionic acid (919361-00-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: nBuLi / diethyl ether; tetrahydrofuran / -78 °C

1.2: 72 percent / diethyl ether; tetrahydrofuran / 1 h / 0 °C

2.1: 100 percent / NaBH₄ / methanol / 1 h / 20 °C

3.1: 100 percent / (COCl)2 / dimethylformamide; CH₂Cl₂ / 3 h / 20 °C

4.1: 75 percent / NaI / acetone / 4 h / 20 °C

5.1: NaHMDS / tetrahydrofuran / 3 h / -50 °C

6.1: LiOH / tetrahydrofuran; methanol; H₂O / 16 h / 20 °C

With lithium hydroxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; sodium hexamethyldisilazane; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 4.1: Finkelstein reaction;

DOI:10.1016/j.bmcl.2006.08.110

upstream raw materials:

5-formyl-2-[2-(5-methyl-2-phenyl-4-oxazolyl)-ethoxy]pyridine

5-bromo-2-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridine

5-(chloromethyl)-2-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridine

{6-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridin-3-yl}methanol

Downstream raw materials:

(S)-4-Benzyl-3-((S)-2-{6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-pyridin-3-ylmethyl}-tetrahydro-furan-2-carbonyl)-oxazolidin-2-one