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Chemical Structure| 137234-62-9 Chemical Structure| 137234-62-9
Chemical Structure| 137234-62-9

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CAS No.: 137234-62-9

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Voriconazole is a second-generation triazole antifungal used to treat serious fungal infections by inhibiting the synthesis of ergosterol, the major sterol of the fungal cell membrane.

Synonyms: UK-109496; DRG 0301; Vfend

4.5 *For Research Use Only !

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Product Details of [ 137234-62-9 ]

CAS No. :137234-62-9
Formula : C16H14F3N5O
M.W : 349.31
SMILES Code : O[C@@]([C@@H](C)C1=NC=NC=C1F)(CN2N=CN=C2)C(C(F)=C3)=CC=C3F
Synonyms :
UK-109496; DRG 0301; Vfend
MDL No. :MFCD00905717
InChI Key :BCEHBSKCWLPMDN-VQVVDHBBSA-N
Pubchem ID :69155711

Safety of [ 137234-62-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H360
Precautionary Statements:P501-P270-P202-P201-P264-P280-P308+P313-P301+P310+P330-P405
Class:6.1
UN#:2811
Packing Group:Ⅲ

Application In Synthesis [ 137234-62-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 137234-62-9 ]

[ 137234-62-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 188416-20-8 ]
  • [ 35963-20-3 ]
  • [ 137234-62-9 ]
YieldReaction ConditionsOperation in experiment
Preparation of Voriconazole Camphorsulfonate (wet) from Hydrochloride Salt of (2R,3S/2S,3R)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol. Hydrochloride salt of (2R,3S/2S,3R)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (180 gm) obtained from Step III of Example 1 or Example 2 or Example 3 was added to methanol (720 mL) at 20 C.-25 C. followed by pH adjustment (8.0-9.0) with 40% w/v aqueous sodium hydroxide solution (50 mL) under nitrogen blanketing. To this reaction mixture, ammonium formate (108.2 gm) was added followed by addition of wet palladium/carbon [Pd/C (2.5% w/w dry, 18 gm)] treated with de-ionized water. The reaction mixture was further heated and stirred at 55 C.-60 C. followed by cooling of the mixture to 30 C.-35 C. The reaction mixture was filtered through hyflobed and washed with methanol (360 mL) first and then with a mixture of de-ionized water (1800 mL) and dichloromethane (900 mL) at 15 C.-20 C. followed by stirring. To the organic layer, de-ionized water (360 mL) was added followed by pH adjustment with 2N hydrochloric acid solution (6 mL) at the same temperature. The solvent was recovered under reduced pressure at 40 C.-45 C. to give residual solid. To the residue acetone (2700 mL) was added followed by addition of the methanolic solution of (1R)-(-)-10-camphorsulfonic acid (99.5 gm in 900 mL methanol) at 40 C.-45 C. Seed of voriconazole camphorsulfonate (0.18 gm) was added to the reaction mixture and the mixture stirred at 40 C.-45 C. for 60 minutes. The slurry so obtained was cooled to 30 C.-35 C. followed by further cooling to 20 C.-25 C. The mixture was stirred for 10-12 hours at 20 C.-25 C. followed by filtration and washing with acetone (180 mL) to give wet voriconazole camphorsulfonate. Wet wt: 91 gm. Voriconazole camphorsulfonate (wet) (entire quantity from Step 4A of Example 4) was added to a stirred mixture of de-ionized water (360 mL) and dichloromethane (360 mL) at 15 C.-25 C. followed by pH adjustment of the mixture to pH 10-11 with 40% w/v aqueous sodium hydroxide solution (16.2 mL). The organic layer was washed with de-ionized water (360 mL) followed by filtration of organic layer through 0.45 micron filter. The filtered layer was further washed with dichloromethane (90 mL) and solvent was recovered under reduced pressure (50-500 torr) at 35 C.-45 C. to give a residual solid. Isopropyl alcohol (450 mL) was added to the residue followed by heating and stirring of the mixture at 60 C.-70 C. until the mixture was dissolved, followed by recovery of isopropyl alcohol under reduced pressure (50-500 torr) at 50 C.-60 C. to obtain a residual volume of 270 mL. The concentrated solution so obtained was heated to 60 C.-70 C. followed by cooling of the solution to 45 C.-50 C. The solution was further cooled to 5 C.-10 C. followed by stirring for 60 minutes at the same temperature. The solid obtained was filtered and washed with isopropyl alcohol (135 mL) followed by drying of the solid under reduced pressure at 50 C.-55 C. until constant weight. %Yield: 42.8%
  • 2
  • [ 188416-20-8 ]
  • [ 137234-62-9 ]
 

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