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Diethyl Ether → N-{3-[3-(3-cyclohexyl-3-oxopropyl)-6-methyl-3-azabicyclo[3.1.0]hex-6-yl]phenyl}methanesulfonamide

HRID 1826366
ノート
印刷プレビュー

反応式

HRID 1826366 の反応式
[CH3:1][C:2]1([C:8]2[CH:9]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:7]2[CH:3]1[CH2:4][NH:5][CH2:6]2.C(=O)([O-])[OH:20].[Na+].[CH:24]1([C:30]2C(CCC=O)=C(S([O-])(=O)=O)C=[CH:34][C:35]=2Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(OCC)C>COC(OC)COCC(OC)OC.O>[NH3:5].[CH:24]1([C:30](=[O:20])[CH2:35][CH2:34][N:5]2[CH2:6][CH:7]3[CH:3]([C:2]3([C:8]3[CH:9]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=3)[CH3:1])[CH2:4]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 22141143N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl)methanesulfonamideHCID 865871903-Cyclohexyl-3-oxopropyl-4-bromobenzenesulfonate

生成物 2

HCID 222AmmoniaHCID 9865947N-{3-[3-(3-cyclohexyl-3-oxopropyl)-6-methyl-3-azabicyclo[3.1.0]hex-6-yl]phenyl}methanesulfonamide
収率 109.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 554377Ethane, 1,1'-oxybis[2,2-dimethoxy-溶媒

反応条件

温度
50 °C

実験手順

To a solution of the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 57 mg, 0.19 mmol) in dimethoxyethyl ether (2 ml) was added sodium hydrogen carbonate (630 mg, 7.52 mmol), and 3-cyclohexyl-3-oxopropyl-4-bromobenzenesulfonate (Preparation 91, 75 mg, 0.2 mmol) and the reaction mixture was heated at 50° C. for 20 h. After cooling, diethyl ether (5 ml) and water (7 ml) were added and the reaction mixture was stirred vigorously for 5 min. The phases were separated and the aqueous layer was further extracted with diethyl ether (2×5 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residual oil was purified by flash column chromatography using a Sep-Pak™ cartridge packed with silica gel (5 g) eluting with dichloromethane:ethanol:0.88 ammonia solution (200:8:1) to afford the title compound as an oil (42 mg, 52%).

後処理

  1. temperatureAfter cooling
  2. customThe phases were separated
  3. extractionthe aqueous layer was further extracted with diethyl ether (2×5 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual oil was purified by flash column chromatography
  8. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-6416b688368c4e31a1e65afd40ce990b
出典データセット
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07049444B2

反応ノート

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