188416-34-4

Basic information

• Product Name: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate
• CAS NO: 188416-34-4
• Molecular Weight: 581.616
• Mol File: 188416-34-4.mol
• Article Data: 8

Chemical Properties

• Density: 1.31[at 20℃]
• Water Solubility: 2.5g/L at 20℃
• CAS DataBase Reference: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate(188416-34-4)
• EPA Substance Registry System: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate(188416-34-4)

Safety Data

• Hazardous Substances Data: 188416-34-4(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

Upstream product

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

IMPROVED PROCESS FOR THE PREPARATION OF (2R,3S)-2-(2,4- DIFLUQROPHENYL)-3-(5-FLUOROPYRIMIDIN-4-YL)-1-(1H-1,2,4-TRIAZOL-1-YL) BUTAN-2-OL

The present invention is directed to an improved industrially viable, cost effective process to manufacture substantially pure form of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (Voriconazole) with a chiral purity level of greater than 99.9% and impurity level of less than 0.1%.