137234-71-0

Basic information

• Product Name: Voriconazole
• Synonyms: (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoropyriMidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol L(-)-CaMphorsulfonate;(2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoropyriMidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol L(-)-CaMphorsulfonate(for Voriconazole);4-PyriMidineethanol, α-(2,4-difluorophenyl)-5-fluoro-β-Methyl-α-(1H-1,2,4-triazol-1-ylMethyl)-, (αR,βS)-, Mono[(1R,4S)-7,7-diMethyl-2-oxobicyclo[2.2.1]heptane-1-Methanesulfonate] (salt);Voriconazole camphor sulfonate;(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol L(-)-camphorsulfonate;(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate;AMYMCJHOGKVJHB-CRFUWKMFSA-N
• CAS NO: 137234-71-0
• Molecular Formula: C₁₀H₁₆O₄S*C₁₆H₁₄F₃N₅O
• Molecular Weight: 581.61
• Product Categories: intermediate
• Mol File: 137234-71-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 127-130℃
• Boiling Point: 508.6°C at 760 mmHg
• Flash Point: 261.4°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 3.63E-11mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: Voriconazole(CAS DataBase Reference)
• NIST Chemistry Reference: Voriconazole(137234-71-0)
• EPA Substance Registry System: Voriconazole(137234-71-0)

Safety Data

• Hazardous Substances Data: 137234-71-0(Hazardous Substances Data)

Usage

General Description

Voriconazole is an antifungal medication used to treat a range of fungal infections. It belongs to the azole class of drugs and works by inhibiting the growth of fungi. Voriconazole is primarily used to treat invasive fungal infections caused by Aspergillus and Candida species, which can affect various body parts including the lungs, bloodstream, and central nervous system. It is available in both oral and intravenous formulations and is commonly prescribed to patients with compromised immune systems, such as those with HIV/AIDS or undergoing organ transplantation. However, as with any medication, Voriconazole can have side effects including visual disturbances, liver toxicity, and skin reactions, so it is important to follow the prescribed dosage and inform healthcare professionals of any pre-existing medical conditions or medications being taken.

InChI:InChI=1/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3

Upstream product

• 188416-20-8 3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride salt 
• 188416-28-6 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane 
• 137234-88-9 4-ethyl-5-fluoropyrimidine 
• 137234-85-6 2,4-dichloro-6-ethyl-5-fluoropyrimidine 
• 137234-74-3 4-chloro-6-ethyl-5-fluoropyrimidine 
• 188416-35-5 3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 906451-64-7 1-(2,4-difluorophenyl)-2-(3,5-dibromo-1H-1,2,4-triazol-1-yl)ethanone 
• 1237497-00-5 6-(1-bromoethyl)-5-fluoropyrimidin-4-yl methanesulfonate 
• 1237496-99-9 6-ethyl-5-fluoropyrimidin-4-yl methanesulfonate 
• 137234-87-8 6-ethyl-5-fluoro-4-hydroxypyrimidine 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 35963-20-3 (R)-10-camphorsulfonic acid 
• 182230-43-9 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 137234-63-0 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol 

Downstream Products

• 137234-62-9 voriconazole 
• 35963-20-3 (R)-10-camphorsulfonic acid 

Relevant articles and documents

Voriconazole synthesis method

The invention relates to a voriconazole synthesis method, which comprises: 1, carrying out catalytic hydrogenation on an SM, anhydrous methanol and anhydrous sodium acetate reaction system by using palladium carbon; after treatment, crystallization is performed to obtain a voriconazole racemate; 2, the voriconazole racemate, an acetone solvent and an L(-)-camphor-10-sulfonic acid system are subjected to a reflux reaction, crystallization and filtration are performed after the reaction is completed, voriconazole camphorsulfonate is obtained, and the molar ratio of L-camphorsulfonic acid to thevoriconazole racemate is 0.5:1; and 3, adjusting the pH value of the voriconazole camphor sulfonate, dichloromethane and water system to 10-11 by using a sodium hydroxide aqueous solution, layering, and temporarily storing an organic phase; extracting the water phase with dichloromethane; and merging the organic phases, carrying out reduced pressure distillation to remove the solvent, and carryingout post-treatment to obtain voriconazole.

PROCESS FOR PREPARING VORICONAZOLE BY USING NEW INTERMEDIATES

Provided is a process for preparing Voriconazole represented by Chemical Formula 1. More particularly, the process for preparing Voriconazole of Chemical Formula 1 includes: carrying out the Reformatsky-type coupling reaction between a ketone derivative of Chemical Formula 4 and a pyrimidine derivative of Chemical Formula 5 to obtain a compound of Chemical Formula 3; reacting the substituents halo and oxysulfonyl with a hydrogen donor to obtain racemicVoriconazole of Chemical Formula 2; and carrying out optical isolation of the racemicVoriconazole by adding an adequate optically active acid thereto to obtain Voriconazole having high optical purity with high cost-efficiency and high yield.

PROCESS FOR PREPARING VORICONAZOLE, NEW POLYMORPHIC FORM OF INTERMEDIATE THEREOF, AND USES THEREOF

The present invention relates to an improved process for preparation of Voriconazole and Voriconazole (1R)-(?)-10-camphorsulfonate.