483340-19-8

Basic information

• Product Name: (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanoic Acid
• Synonyms: (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanoic Acid;Isavuconazole interMediate 4;(2R,3R)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanoic acid
• CAS NO: 483340-19-8
• Molecular Formula: C13H13F2N3O3
• Molecular Weight: 297.2574264
• Mol File: 483340-19-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 191-193 °C(Solv: methanol (67-56-1))
• Boiling Point: 519.9±60.0 °C(Predicted)
• Appearance: /
• Density: 1.43±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DCM, Methanol
• PKA: 3.89±0.23(Predicted)
• CAS DataBase Reference: (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanoic Acid(483340-19-8)
• EPA Substance Registry System: (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanoic Acid(483340-19-8)

Safety Data

• Hazardous Substances Data: 483340-19-8(Hazardous Substances Data)

Usage

Uses

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

Upstream product

• 944473-05-6 (2R,3R)-3-[3-(2,5-difluorophenyl)-3,4-epoxy-2-methyl]butanoic acid 
• 41253-21-8 sodium triazole 
• 1157938-97-0 1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 

Downstream Products

• 241479-67-4 Isavuconazole 
• 241479-74-3 (2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile 
• 241479-75-4 (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide 

Relevant articles and documents

AN IMPROVED PROCESS FOR THE PREPARATION OF TRIAZOLE DERIVATIVES

The present invention relates to an improved process for the preparation of triazole derivatives such as ravuconazole and isavuconazole.

Method for resolving racemic body of intermediate compound of Isavuconazole

The invention discloses a novel method for resolving a racemic body of an intermediate compound of Isavuconazole. According to the novel method, R(+)-alpha-methylbenzylamine is adopted as a resolving reagent, and (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxyl-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanoic acid with high optical purity is obtained. According to the novel method for resolving the racemic body of the intermediate compound of the Isavuconazole, disclosed by the invention, the steps are simple, the yield is relatively high, and (2R, 3R)-3-(2,5-difluorophenyl)-3-hydroxyl-2-methyl-4-(1H-1,2,4-triazol-1-yl) butanoic acid with high optical purity is obtained through resolution; and meanwhile, the resolving reagent, i.e., R(+)-alpha-methylbenzylamine can be recovered and reused, so that the cost is reduced, the implementation of industrialized amplified production is facilitated, and the novel method has a very good industrial application prospect.

Asymmetric zinc-Reformatsky reaction of Evans chiral imide with acetophenones and its application to the stereoselective synthesis of triazole antifungal agents

The Ni(acac)2 catalytic ZnEt2-mediated asymmetric Reformatsky-type reaction of Evans chiral imide with various acetophenones was studied. The chiral imido zinc enolate, which was formed through the metal-halogen exchange reaction of