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

HRID 2181934노트

반응식

HRID 2181934 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

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.;

후처리

  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

출처 및 근거

ORD 기록
ord-9f57048f389445668bd47df358e7dedd
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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