Triethylamine → Voriconazole

HRID 1099525Notes

Reaction equation

HRID 1099525 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(N(CC)CC)C>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 8471TriethylamineHCID 86626425Voriconazole (1R)-(-)-10-camphorsulfonate

Product 1

HCID 71616VoriconazoleYield 78.26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22.5 °C

Procedure

Voriconazole (1R)-(−)-10-camphorsulfonate (1 g, 1.72 mmol, enantiomeric purity 97.18%) was suspended in deionised water (10 ml) and treated with triethylamine (0.24 ml, 1.72 mmol) at 45-55° C. for 3 hours and 30 minutes. The suspension was cooled down to 20-25° C., stirred for 10 minutes and filtered. The cake was washed with deionised water (2×10 ml). The solid was dried under vacuum at 50-55° C. until constant weight (0.47 g, 78.26% yield).

Workup

  1. filtrationfiltered
  2. washThe cake was washed with deionised water (2×10 ml)
  3. customThe solid was dried under vacuum at 50-55° C. until constant weight (0.47 g, 78.26% yield)

Sources & evidence

ORD record
ord-1ba40b98215a440b9c2ccd65617fdbc8
Source dataset
uspto-grants-2012_03
Patent number
US08143397B2

Reaction notes

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