Sodium Bicarbonate → Voriconazole

HRID 1099521Notes

Reaction equation

HRID 1099521 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.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[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 516892Sodium BicarbonateHCID 86626425Voriconazole (1R)-(-)-10-camphorsulfonate

Product 1

HCID 71616VoriconazoleYield 91.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Voriconazole (1R)-(−)-10-camphorsulfonate (6 g, 10.3 mmol) was suspended in ethyl acetate (18 ml) and treated slowly with aqueous saturated solution of sodium bicarbonate (14.4 ml). The mixture was stirred for 10 minutes and allowed to settle. The organic phase was separated and the aqueous phase was re-extracted with ethyl acetate (13.5 ml). The combined organic phases were washed with deionised water (1.8 ml), filtered through paper and concentrated under reduced pressure to give a white solid (3.28 g, 91.11% yield).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was re-extracted with ethyl acetate (13.5 ml)
  3. washThe combined organic phases were washed with deionised water (1.8 ml)
  4. filtrationfiltered through paper
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c5bf0f15f59488483a12cee9edf4d56
Source dataset
uspto-grants-2012_03
Patent number
US08143397B2

Reaction notes

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