(2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Base Information

• Chemical Name: (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide
• CAS No.: 1312479-51-8
• Molecular Formula: C₂₂H₂₇FN₂O₆S
• Molecular Weight: 466.531
• Mol file: 1312479-51-8.mol

Synonyms:(2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Chemical Property of (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

There total 8 articles about (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide 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: 90.9%

→ (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (1312479-51-8)

Guidance literature:

Reference yield: 75.0%

O-2-tetrahydro-2H-pyranhydroxylamine (6723-30-4) + ethyl (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoic acid (1312479-50-7) → (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (1312479-51-8)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane;

DOI:10.1021/jm2014875

Reference yield:

ethyl (±)-4-bromo-2-methyl-2-(methylsulfonyl)butanoate (1312478-47-9) → (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (1312479-51-8)

Guidance literature:

Multi-step reaction with 5 steps

1: ethanol / 0.02 h / Resolution of racemate

2: caesium carbonate / tetrahydrofuran; tert-butyl alcohol / 70 °C

3: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 2-methyltetrahydrofuran; water / 1 h / 60 °C

4: potassium hydroxide / 2-methyltetrahydrofuran; water / 20 °C

5: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine / dichloromethane

With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; benzotriazol-1-ol; caesium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; potassium hydroxide; In tetrahydrofuran; 2-methyltetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol; 3: Suzuki-Miyaura coupling;

DOI:10.1021/jm2014875

upstream raw materials:

O-2-tetrahydro-2H-pyranhydroxylamine

ethyl (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoic acid

ethyl (±)-4-bromo-2-methyl-2-(methylsulfonyl)butanoate

(2R)-ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate

Downstream raw materials:

(2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide