(αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanaMide

Base Information

• Chemical Name: (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanaMide
• CAS No.: 241479-75-4
• Molecular Formula: C₁₃H₁₄F₂N₄O₂
• Molecular Weight: 296.277
• Mol file: 241479-75-4.mol

Synonyms:

Chemical Property of (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanaMide

Chemical Property:

• Boiling Point: 581.9±60.0 °C(Predicted)
• PKA: 11.52±0.29(Predicted)
• Density: 1.43±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility.: Methanol, DCM

Purity/Quality:

98%,99%, ^*data from raw suppliers

(αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-methyl-1H-1,2,4-triazole-1-butanamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-methyl-1H-1,2,4-triazole-1-butanamide is an intermediate in the synthesis of Isavuconazole (I777830), an triazole based antifungal agent for the treatment of invasive fungal infections.

Technology Process of (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanaMide

There total 4 articles about (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-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:

(2R,3R)-3-[3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-3-(1H-1,2,4-triazol-1-yl)]butanoic acid (483340-19-8) → (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide (241479-75-4)

Guidance literature:

(2R,3R)-3-[3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-3-(1H-1,2,4-triazol-1-yl)]butanoic acid; With thionyl chloride; In tetrahydrofuran; at 35 - 40 ℃;

With ammonia; In tetrahydrofuran; at 5 - 10 ℃; for 2h; Temperature; Solvent; Reagent/catalyst;

Reference yield:

3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanoic acid (483340-19-8) → (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide (241479-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (S)-1-phenyl-ethylamine / methanol / 60 - 80 °C

2.1: thionyl chloride / tetrahydrofuran / 35 - 40 °C

2.2: 2 h / 5 - 10 °C

With thionyl chloride; (S)-1-phenyl-ethylamine; In tetrahydrofuran; methanol;

Reference yield:

1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (1157938-97-0) → (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide (241479-75-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: chloro-trimethyl-silane; zinc; iodine / tetrahydrofuran / 16 h / 50 - 70 °C / Inert atmosphere

2.1: sodium hydroxide; water / methanol / 25 - 30 °C

3.1: (S)-1-phenyl-ethylamine / methanol / 60 - 80 °C

4.1: thionyl chloride / tetrahydrofuran / 35 - 40 °C

4.2: 2 h / 5 - 10 °C

With chloro-trimethyl-silane; thionyl chloride; (S)-1-phenyl-ethylamine; water; iodine; sodium hydroxide; zinc; In tetrahydrofuran; methanol;

upstream raw materials:

3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanoic acid

1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

(2R,3R)-3-[3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-3-(1H-1,2,4-triazol-1-yl)]butanoic acid

Downstream raw materials:

(2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile

Isavuconazole

Refernces