Sodium Hydroxide → Voriconazole

HRID 1099522Notes

Reaction equation

HRID 1099522 reaction equation
[CH3:1][C@H:2]([C@@:10]([OH:25])([C:17]1[CH:18]=[CH:19][C:20]([F:24])=[CH:21][C:22]=1[F:23])[CH2:11][N:12]1[N:16]=[CH:15][N:14]=[CH:13]1)[C:3]1[N:8]=[CH:7][N:6]=[CH:5][C:4]=1[F:9].[C@@]12(CS([O-])(=O)=O)C(C)(C)C(CC1)CC2=O.[OH-].[Na+]>O>[CH3:1][C@H:2]([C@@:10]([OH:25])([C:17]1[CH:18]=[CH:19][C:20]([F:24])=[CH:21][C:22]=1[F:23])[CH2:11][N:12]1[N:16]=[CH:15][N:14]=[CH:13]1)[C:3]1[N:8]=[CH:7][N:6]=[CH:5][C:4]=1[F:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86626425Voriconazole (1R)-(-)-10-camphorsulfonate

Product 1

HCID 71616VoriconazoleYield 87.22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22.5 °C

Procedure

Voriconazole (1R)-(−)-10-camphorsulfonate (1 g, 1.72 mmol) was suspended in deionised water (10 ml) and treated with 5 N NaOH (0.34 ml, 1.72 mmol) at 45-55° C. for 2 hours and 30 minutes. The suspension was cooled down to 20-25° C., stirred for 15 minutes and filtered. The cake was washed with deionised water (15 ml). The solid was dried at 50-60° C. under vacuum until constant weight (0.523 g, 87.22% yield).

Workup

  1. filtrationfiltered
  2. washThe cake was washed with deionised water (15 ml)
  3. customThe solid was dried at 50-60° C. under vacuum until constant weight (0.523 g, 87.22% yield)

Sources & evidence

ORD record
ord-ecde280408984f4393168815a722be11
Source dataset
uspto-grants-2012_03
Patent number
US08143397B2

Reaction notes

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