Voriconazole → Voriconazole (1R)-(-)-10-camphorsulfonate

HRID 1099519Notes

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@@:26]12([CH2:36][S:37]([OH:40])(=[O:39])=[O:38])[C:33]([CH3:35])([CH3:34])[CH:30]([CH2:31][CH2:32]1)[CH2:29][C:27]2=[O:28]>CO>[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@@:26]12([CH2:36][S:37]([O-:40])(=[O:38])=[O:39])[C:33]([CH3:35])([CH3:34])[CH:30]([CH2:31][CH2:32]1)[CH2:29][C:27]2=[O:28]

Participants

Conditions

Temperature: 52.5 °C

Procedure

A mixture of racemic Voriconazole (5 g, 14.3 mmol) and (1R)-(−)-10-camphorsulfonic acid (3.33 g, 14.3 mmol) in methanol (50 ml) was heated until solution at 50-55° C. The solution was cooled down to 22-24° C., stirred for 2 hours and filtered. A white crystalline solid was isolated.

Workup

temperatureThe solution was cooled down to 22-24° C.
filtrationfiltered
customA white crystalline solid was isolated

Sources & evidence

ORD record: ord-5d86cad4d7004db2a4aa726c30e2300a
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143397B2

Reaction notes

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