Sodium Carbonate → Voriconazole

HRID 1099529Notes

Reaction equation

HRID 1099529 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+].[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 10340Sodium CarbonateHCID 86626425Voriconazole (1R)-(-)-10-camphorsulfonate

Product 1

HCID 71616VoriconazoleYield 93.49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22.5 °C

Procedure

Voriconazole (1R)-(−)-10-camphorsulfonate from example 12 (11 g, 18.9 mmol, enantiomeric purity 100%) was suspended in deionised water (110 ml) and treated with aqueous 10% w/v Na2CO3 (20.4 ml, 18.9 mmol) at 45-55° C. for 2 hours and 30 minutes. The suspension was cooled down to 20-25° C. and filtered. The cake was washed with deionised water (2×20 ml). The solid was dried at 50-60° C. under vacuum until constant weight (6.18 g, 93.49% yield).

Workup

  1. additiontreated with aqueous 10%
  2. customat 45-55° C.
  3. customfor 2 hours
  4. custom30 minutes
  5. filtrationfiltered
  6. washThe cake was washed with deionised water (2×20 ml)
  7. customThe solid was dried at 50-60° C. under vacuum until constant weight (6.18 g, 93.49% yield)

Sources & evidence

ORD record
ord-86f862b820b740da8168a4759ba5f9d8
Source dataset
uspto-grants-2012_03
Patent number
US08143397B2

Reaction notes

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