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

HRID 2181934ノート

反応式

HRID 2181934 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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.;

後処理

  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

出典と根拠

ORDレコード
ord-9f57048f389445668bd47df358e7dedd
出典データセット
uspto-grants-2005_05
特許番号
US06894061B2

反応ノート

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