(αR)-4-(2-Fluoro-4-Methoxyphenyl)-N-hydroxy-α-Methyl-α-(Methylsulfonyl)-2-oxo-1(2H)-pyridinebutanaMide

Base Information

• Chemical Name: (αR)-4-(2-Fluoro-4-Methoxyphenyl)-N-hydroxy-α-Methyl-α-(Methylsulfonyl)-2-oxo-1(2H)-pyridinebutanaMide
• CAS No.: 1312473-63-4
• Molecular Formula: C18H21FN2O6S
• Molecular Weight: 412.439
• Mol file: 1312473-63-4.mol

Synonyms:(αR)-4-(2-Fluoro-4-Methoxyphenyl)-N-hydroxy-α-Methyl-α-(Methylsulfonyl)-2-oxo-1(2H)-pyridinebutanaMide;PF-5081090;(2R)-4-[4-(2-Fluoro-4-methoxyphenyl)-2-oxo-2H-pyridin-1-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;PF 05081090;(R)-4-(4-(4-(2H-1,2,3-triazol-2-yl)phenyl)-2-oxopyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

Chemical Property of (αR)-4-(2-Fluoro-4-Methoxyphenyl)-N-hydroxy-α-Methyl-α-(Methylsulfonyl)-2-oxo-1(2H)-pyridinebutanaMide

Chemical Property:

• PKA: 8.11±0.50(Predicted)
• PSA: 126.57000
• Density: 1.378±0.06 g/cm3(Predicted)
• LogP: 3.28290
• Storage Temp.: room temp
• Solubility.: DMSO: >5mg/mL (warmed)

Purity/Quality:

97% ^*data from raw suppliers

PF-5081090 ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: PF-5081090 is a pyridone methylsulfone hydroxamate LpxC inhibitor. PF-5081090 is used as an antibiotic in the treatment of serious gram-negative infections.

Technology Process of (αR)-4-(2-Fluoro-4-Methoxyphenyl)-N-hydroxy-α-Methyl-α-(Methylsulfonyl)-2-oxo-1(2H)-pyridinebutanaMide

There total 8 articles about (αR)-4-(2-Fluoro-4-Methoxyphenyl)-N-hydroxy-α-Methyl-α-(Methylsulfonyl)-2-oxo-1(2H)-pyridinebutanaMide 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: 91.0%

(2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (1312478-99-1) → (2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (1312473-63-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; dichloromethane; at 20 ℃;

DOI:10.1021/jm2014875

Reference yield:

ethyl (2R)-4-(4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate (1312479-77-8) → (2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (1312473-63-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 2-methyltetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere

1.2: 1 h / 55 °C

2.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / 2-methyltetrahydrofuran / 1.42 h / Inert atmosphere

2.2: 0.75 h

3.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 75 °C

With 4-methyl-morpholine; potassium phosphate; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; pyridinium p-toluenesulfonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 2-methyltetrahydrofuran; ethanol; water;

Reference yield:

(2-fluoro-4-methoxyphenyl)boronic acid (162101-31-7) → (2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (1312473-63-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 2-methyltetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere

1.2: 1 h / 55 °C

2.1: 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine / 2-methyltetrahydrofuran / 1.42 h / Inert atmosphere

2.2: 0.75 h

3.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 75 °C

With 4-methyl-morpholine; potassium phosphate; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; pyridinium p-toluenesulfonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 2-methyltetrahydrofuran; ethanol; water;

upstream raw materials:

(2-fluoro-4-methoxyphenyl)boronic acid

(2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoic acid

(2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

ethyl (2R)-4-(4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

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