Water → 4-{[(6S)-8-Fluoro-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenyl sulfamate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:5]2[CH3:26].[S:27](Cl)(=[O:30])(=[O:29])[NH2:28].O>CC(N(C)C)=O>[S:27](=[O:30])(=[O:29])([O:25][C:22]1[CH:21]=[CH:20][C:19]([S:16]([N:6]2[C@@H:5]([CH3:26])[C:4]3[C:13](=[CH:14][CH:15]=[C:2]([F:1])[CH:3]=3)[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)(=[O:18])=[O:17])=[CH:24][CH:23]=1)[NH2:28]Participants
Procedure
To a stirred solution of 4-{[(6S)-8-fluoro-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol (1.11 g, 3.0 mmol) in dimethyacetamide (10 mL), cooled to 0° C., was added sulfamoyl chloride (1.39 g, 12.0 mmol). The mixture was allowed to warm to room temperature and stirring continued for 16 hours. Water (100 mL) was added and a white precipitate deposited on the inside of the reaction vessel. The water was removed and the flask was washed with additional water. The white solid was dissolved in dichloromethane and purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 30% -50% methyl tert-butyl ether in hexane, to afford the title compound (1.16 g, 87% ) as a white solid, m.p.
Workup
- customThe water was removed
- washthe flask was washed with additional water
- dissolutionThe white solid was dissolved in dichloromethane
- custompurified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
- washeluting with a gradient of 30% -50% methyl tert-butyl ether in hexane
Sources & evidence
- ORD record
- ord-29c6a5a5cfca46b89d83987cd3766a37
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378427B2
Reaction notes
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