Water → 4-{[(6S)-8-Fluoro-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenyl sulfamate

HRID 2181934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181934
[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]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24499Chlorosulfamic acidHCID 104742374-{[(S)-8-fluoro-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol

Produkt 1

HCID 692557444-{[(6S)-8-Fluoro-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenyl sulfamateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

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. 166.5-167° C.;

Aufarbeitung

  1. customThe water was removed
  2. washthe flask was washed with additional water
  3. dissolutionThe white solid was dissolved in dichloromethane
  4. custompurified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  5. washeluting with a gradient of 30%-50% methyl tert-butyl ether in hexane

Quellen und Nachweise

ORD-Eintrag
ord-9f57048f389445668bd47df358e7dedd
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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