137234-63-0

Basic information

• Product Name: ent-Voriconazole
• Synonyms: ent-Voriconazole;(αS,βR)-α-(2,4-Difluorophenyl)-5-fluoro-β-Methyl-α-(1H-1,2,4-triazol-1-ylMethyl)-4-pyriMidineethanol;(alphaS,betaR)-alpha-(2,4-Difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol;epi-Voriconazole;Voriconazole impurity D
• CAS NO: 137234-63-0
• Molecular Formula: C16H14F3N5O
• Molecular Weight: 349.3104696
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 137234-63-0.mol
• Article Data: 40

Chemical Properties

• Melting Point: 130-132°C
• Boiling Point: 508.6±60.0 °C(Predicted)
• Appearance: /
• Density: 1.42±0.1 g/cm3(Predicted)
• Storage Temp.: -20?C Freezer
• PKA: 11.54±0.29(Predicted)
• CAS DataBase Reference: ent-Voriconazole(CAS DataBase Reference)
• NIST Chemistry Reference: ent-Voriconazole(137234-63-0)
• EPA Substance Registry System: ent-Voriconazole(137234-63-0)

Safety Data

• Hazardous Substances Data: 137234-63-0(Hazardous Substances Data)

Usage

Description

Ent-Voriconazole, also known as the (2S,3R) enantiomer in Voriconazole (V760000) drug substance, is a white solid with distinct chemical properties. It is one of the two mirror-image isomers of Voriconazole, a well-known antifungal medication. Ent-Voriconazole possesses unique characteristics that make it a potential candidate for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
Ent-Voriconazole is used as an active pharmaceutical ingredient (API) for its antifungal properties. It is particularly effective against a wide range of fungal infections, including those caused by Aspergillus and Candida species. The enantiomer's specific properties may also contribute to the development of new drugs with improved efficacy and reduced side effects.
Used in Research and Development:
In the field of research and development, ent-Voriconazole is used as a key compound for studying the effects of stereochemistry on drug action. Its unique properties allow scientists to explore the differences in biological activity between enantiomers, which can lead to the discovery of more effective and safer medications.
Used in Drug Delivery Systems:
Ent-Voriconazole can be employed as a component in the development of novel drug delivery systems, such as nanoparticles or liposomes. These systems aim to improve the drug's bioavailability, targeting, and overall therapeutic outcomes by enhancing its solubility, stability, and controlled release.
Used in Cosmetic Industry:
Due to its antifungal properties, ent-Voriconazole can be used as an additive in the cosmetic industry for products targeting fungal infections, such as dandruff shampoos or antifungal creams. Its inclusion in these products can help improve their efficacy in treating and preventing fungal-related skin conditions.
Used in Agricultural Industry:
Ent-Voriconazole's antifungal properties can also be harnessed in the agricultural industry for the protection of crops from fungal diseases. By incorporating the enantiomer into fungicides or other protective agents, it can help reduce the impact of fungal infections on crop yields and quality.

Upstream product

• 759-67-1 2-fluoro-3-oxopentanoic acid ethyl ester 
• 137234-87-8 6-Ethyl-5-fluoropyrimidin-4(3H)-one 
• 137234-74-3 4-chloro-6-ethyl-5-fluoropyrimidine 
• 188416-28-6 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane 
• 86404-63-9 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone 
• 1474024-65-1 (R)-((R)-2-(2,4-difluorophenyl)oxiran-2-yl)(5-fluoropyrimidin-4-yl)methanol 
• 1474024-66-2 (R)-(2-(2,4-difluorophenyl)oxiran-2-yl)(5-fluoropyrimidin-4-yl)-methanone 
• 1474024-67-3 (R)-4-(1-(2-(2,4-difluorophenyl)oxirane-2-yl)vinyl)-5-fluoropyrimidine 
• 288-88-0 1,2,4-Triazole 
• 1474024-68-4 4-((S)-1-((R)-2-(2,4-difluorophenyl)oxirane-2-yl)ethyl)-5-fluoropyrimidine 
• 1403893-61-7 4-chloro-5-fluoro-6-vinylpyrimidine 
• 898044-55-8 4-chloro-5-fluoro-6-methylpyrimidine 
• 861718-85-6 3-chloro-2-(2,4-difluorophenyl)-2-(trimethylsilanyloxy)propionaldehyde 
• 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

• 1631143-19-5 C₁₆H₁₄F₃N₅O*C₇H₆O₃ 
• 1631143-18-4 C₁₆H₁₄F₃N₅O*C₇H₇NO₂ 
• 1631143-20-8 C₁₆H₁₄F₃N₅O*C₇H₅NO₄ 
• 1620283-07-9 C₁₆H₁₃F₃N₆O₃ 
• 1620283-08-0 C₁₆H₁₅F₃N₆O 
• 1620283-05-7 C₂₀H₁₉F₃N₆O₄ 
• 1620283-09-1 C₂₄H₂₂F₃N₇O₆ 
• 1620283-06-8 C₁₉H₁₉F₂N₇O₅ 

Relevant articles and documents

Voriconazole synthesis process

The invention discloses a synthesis process of voriconazole bulk drug, which comprises the following steps: preparing halogenated ethyl fluorouracil and carrying out Grignard reaction. 2 - (2, 4 - Difluorophenyl) -3 - (1, 2, 4 - triazol -1 -yl) -1, 2 - propylene glycol was oxidized to give a propylene oxide compound. The Grignard reagent and the propylene oxide compound are mixed and reacted to obtain voriconazole. To the synthesis process, the reaction steps can be simplified, the dehydrochlorination and hydrogenolysis of palladium carbon are not needed, the reaction period is shortened, and furthermore, the energy consumption is reduced, the cost is reduced, and voriconazole and the racemate thereof are obtained with higher yield.

Synthesis method of voriconazole and intermediate of voriconazole

The invention relates to a synthesis method of voriconazole and an intermediate of voriconazole. The synthesis method comprises the following step: in a protective gas atmosphere, reacting a compoundshown in formula I and a compound shown in formula II in an organic solvent under the action of a metal catalyst, N-heterocyclic carbene, samarium diiodide and elemental iodine to obtain the voriconazole intermediate shown in formula III. According to the synthesis method of the voriconazole intermediate, under the action of the metal catalyst and SmI2, N-heterocyclic carbene is simultaneously added as a ligand, and elemental iodine is used as an initiator to initiate a reformask coupling reaction between the compound shown in formula I and the compound shown in formula II, so that the defectsof low yield, more byproducts and the like of the traditional reaction are overcome, and the yield and the purity are further improved.

Preparation method of voriconazole intermediate

The invention is suitable for the technical field of chemical synthesis and medicine, and provides a preparation method of voriconazole intermediate, which comprises steps of: carrying out a bromination reaction on 4-chloro-6-ethyl-fluoropyrimidine, N-bromosuccinimide, azodiisobutyronitrile and a first solvent to obtain a first intermediate; carrying out condensation reaction on the first intermediate, 2',4'-difluoro-2-[1-(1H-1,2,4-triazolyl)]acetophenone, zinc powder subjected to acid treatment and a second solvent to obtain a second intermediate; mixing the second intermediate, a third solvent and potassium formate to obtain a mixed solution; and adding palladium carbon into the mixed solution, and carrying out reflux reaction in a protective atmosphere to obtain the voriconazole intermediate. According to the preparation method disclosed by the invention, the voriconazole intermediate with high yield and high purity can be prepared.