170862-36-9

Basic information

• Product Name: [R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile
• Synonyms: (αS,βR)-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile;[R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile;(2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-Methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile;(alphaS,betaR)-beta-(2,4-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanenitrile
• CAS NO: 170862-36-9
• Molecular Formula: C₁₃H₁₂F₂N₄O
• Molecular Weight: 278.2573864
• Mol File: 170862-36-9.mol

Chemical Properties

• Melting Point: 178-182 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 522.5±60.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.15±0.29(Predicted)
• CAS DataBase Reference: [R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: [R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile(170862-36-9)
• EPA Substance Registry System: [R-(R*,S*)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile(170862-36-9)

Safety Data

• Hazardous Substances Data: 170862-36-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[R-(R,S)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile is used as an intermediate in the synthesis of triazole antifungal agents for the pharmaceutical industry. Its unique structure and properties make it a valuable component in the development of new antifungal drugs, potentially offering improved efficacy and reduced side effects compared to existing treatments.
Used in Chemical Research:
As a complex and potentially bioactive molecule, [R-(R,S)]-β-(2,4-Difluorophenyl)-β-hydroxy-α-Methyl-1H-1,2,4-triazole-1-butanenitrile may also be used in chemical research for the development of new compounds with various applications, such as pharmaceuticals, agrochemicals, or materials science. Its chirality and structural features could provide a foundation for the design of novel molecules with specific biological activities or material properties.

Upstream product

• 219872-85-2 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide 
• 86404-63-9 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone 
• 166948-49-8 (2R,3R)-3-[3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-3-(1H-1,2,4-triazol-1-yl)]butanoic acid 
• 861718-85-6 3-chloro-2-(2,4-difluorophenyl)-2-(trimethylsilanyloxy)propionaldehyde 
• 861718-83-4 (S)-3-chloro-2-(2,4-difluorophenyl)-2-((trimethylsilyl)oxy)propanenitrile 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 132507-89-2 (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 7677-24-9 trimethylsilyl cyanide 
• 124627-86-7 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 
• 1188327-50-5 diethylaluminium cyanide 
• 170862-51-8 (2R,3S)-2-(2,4-Difluoro-phenyl)-3-methyl-1-[1,2,4]triazol-1-yl-4-trityloxy-butan-2-ol 
• 170862-54-1 (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-4-triphenylmethyloxy-1,2-butanediol 
• 170862-47-2 (S)-1-(2,4-Difluoro-phenyl)-2-methyl-3-trityloxy-propan-1-one 
• 170862-53-0 (2S,3R)-3-(2,4-difluorophenyl)-2-methyl-4-(1H-1,2,4-triazol-1-yl)butane-1,3-diol 

Downstream Products

• 170863-34-0 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide 
• 1175536-51-2 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide hydrosulfate 
• 219872-85-2 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide 
• 182760-06-1 ravuconazole 
• 207224-81-5 (2R,3R)-2-(2,4-Difluoro-phenyl)-3-{4-[4-(2H-tetrazol-5-yl)-phenyl]-thiazol-2-yl}-1-[1,2,4]triazol-1-yl-butan-2-ol 
• 207224-83-7 (2R,3R)-2-(2,4-Difluoro-phenyl)-1-[1,2,4]triazol-1-yl-3-{4-[4-(1H-[1,2,4]triazol-3-yl)-phenyl]-thiazol-2-yl}-butan-2-ol 
• 368421-60-7 4-{2-[(1R,2R)-2-(2,4-Difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-thiazol-4-yl}-thiobenzamide 
• 170863-35-1 (2R,3R)-2-(2,4-Difluoro-phenyl)-3-[4-(4-methylsulfanyl-phenyl)-thiazol-2-yl]-1-[1,2,4]triazol-1-yl-butan-2-ol 

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 manufacturing isavuconazole or ravuconazole

The invention provides a method for manufacturing a triazole compound isavuconazole or ravuconazole which is enriched by a diastereoisomer and enantiomer. The method comprises the following steps: a Reformatsky reaction is carried out between ketone and dihalogeno metal propionitrile; an enantiomer mixture is generated, and separation is carried out. The method can obviously reduce steps for synthesis of isavuconazole or ravuconazole, yield of products is improved, and production cost is reduced.

An enantioselective synthesis of the key intermediate for triazole antifungal agents; Application to the catalytic asymmetric synthesis of efinaconazole (jublia)

A new synthetic route, the shortest reported to date, to access a key intermediate for the synthesis of various triazole antifungal agents was developed. The elusive tetrasubstituted stereogenic center that is essential in advanced triazole antifungal agents was constructed via the catalytic asymmetric cyanosilylation of a ketone. The subsequent transformations were performed in two one-pot operations, enhancing the overall synthetic efficiency toward the intermediate. This streamlined synthetic approach was successfully applied to efficient enantioselective syntheses of efinaconazole (Jublia) and ravuconazole.

Improved chiral synthesis of ravuconazole

A short, elegant, and high yielding synthesis of ravoconazole is presented. The key step of this synthesis is an enantioselective palladium-catalyzed chiral zinc-allene addition reaction. The starting materials are 2-chloro-1-(2,4-difluorophenyl)-ethanone and (R)-4-phenylbutyn-2-ol obtained from enzymatic resolution of its racemate. Copyright Taylor & Francis Group, LLC.

The process development of ravuconazole: An efficient multikilogram scale preparation of an antifungal agent

The development of a safe, robust process for the preparation of ravuconazole (1), an antifungal agent, is described. The discovery and development of procedures enabling the efficient synthesis of multikilogram quantities of 1 and the process demonstration through plant scale preparations are presented. A controlled means to prepare a Grignard reagent and utilization of Fourier Transform Infrared spectroscopy (FTIR) monitoring to safely conduct the reaction is featured.

Azole antifungal agents, processes for the preparation thereof, and intermediates

A compound represented by the general formula: wherein R1 and R2 denote a halogen atom or hydrogen atoms; R3 means a hydrogen atoms or lower alkyl group; r and m stand for 0 or 1; A is N or CH; W denotes an aromatic ring or a condensed ring thereof; X means another aromatic rings, an alkanediyl group, an alkenediyl group, or an alkynediyl group; Y stand for -S-, etc.; Z denotes a hydrogen atom, etc., or a salt thereof, and intermediates thereof or a salt thereof as well as processes for the preparation thereof, and pharmacetical composition suitable for use as an antifungal agent.

Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives

A series of novel thiazole-containing triazole antifungals was synthesized and evaluated for antifungal activity against a variety of clinically isolated pathogenic fungi in vitro and against systemic candidosis in vivo. These compounds showed potent antifungal activities in vitro and in vivo. In particular, (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4- difluorophenyl)-1-(1H-1,2,4-triazol-l-yl)-2-butanol (12g; ER-30346) showed potent and well-balanced in vitro activities and potent in vivo efficacy, and had a good safety profile.

A novel route for chiral synthesis of the triazole antifungal ER-30346

A novel synthetic route to (2S,3S)-2-(2,4-difluorophenyl)-3-hydroxy-2- methyl-4-(1-(1,2,4-triazolyl))butyronitrile (2), an intermediate for the orally active triazole antifungal agent ER-30346, was developed from methyl S-(+)-3-hydroxy-2-methylpropionate,

Synthesis of 14C-labelled ER-30346, a novel antifungal triazole

ER-30346 is a new orally active antifungal triazole which has potent, broad spectrum antifungal activity, and good safety profile. It was synthesized labelled in the phenyl ring of the benzonitrile moiety with carbon-14, starting from 4-acetyl[ring-U-14C]benzonitrile, according to the method illustrated in Scheme 1. 14C-labelled ER-30346 having a specific activity of 1.89 Bq/mmol was obtained in 65.4% overall radiochemical yield, with a radiochemical purity of 99.7%.

Practical oxirane ring opening with in situ prepared LiCN; synthesis of (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)-1 -butanenitrile

Trisubstituted oxirane 1 was regiospecifically opened with LiCN in situ prepared from acetone cyanohydrin and LiH to provide the corresponding β-hydroxy nitrile 2 in satisfactory yield, enabling us to manufacture a key intermediate for a new antifungal agent on a multi-kg scale. Some applications of this method to the ring opening of other oxiranes and nucleophilic substitution are also described.