Triethylamine → Voriconazole

HRID 1099526Notes

Reaction equation

HRID 1099526 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 92.13%

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 100.0%) was suspended in deionised water (110 ml) and treated with triethylamine (2.90 ml, 20.8 mmol) at 45-55° C. for 3 hours. 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 under vacuum at 50-60° C. until constant weight (6.09 g, 92.13% yield).

Workup

  1. filtrationfiltered
  2. washThe cake was washed with deionised water (2×20 ml)
  3. customThe solid was dried under vacuum at 50-60° C. until constant weight (6.09 g, 92.13% yield)

Sources & evidence

ORD record
ord-a1c2ad0100d94a5f863de8966aa029aa
Source dataset
uspto-grants-2012_03
Patent number
US08143397B2

Reaction notes

Loading…