Sulfuric Acid → 3-Bromo-6,6-dimethyl-9-((2R,3R)-2,3,4-trihydroxy-butoxy)-5,6-dihydro-benzo[b]carbazol-11-one

HRID 2275185ノート

反応式

HRID 2275185 の反応式
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:39])[C:8]4[CH:20]=[C:19]([O:21][CH2:22][C@@H:23]5[C@H:27]([C:28](C)(C)[O:29][SiH2]C(C)(C)C)[O:26]C(C)(C)[O:24]5)[CH:18]=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:39])[C:8]4[CH:20]=[C:19]([O:21][CH2:22][C@@H:23]([OH:24])[C@H:27]([OH:26])[CH2:28][OH:29])[CH:18]=[CH:17][C:9]=4[C:10]([CH3:15])([CH3:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 131733423HCID 131733423、化合物

生成物 1

HCID 668346893-Bromo-6,6-dimethyl-9-((2R,3R)-2,3,4-trihydroxy-butoxy)-5,6-dihydro-benzo[b]carbazol-11-one収率 82%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

3-Bromo-9-[(4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound JJ7-1, 13.7 mg, 0.0223 mmol) was dissolved in THF (0.15 mL) and methanol (0.1 mL), added with 0.5 M sulfuric acid (0.05 mL), and then stirred at 60° C. for 3 hr. After cooling, the reaction solution was added with saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. After filtration and the concentration under reduced pressure, the resulting solid was washed with dichloromethane to obtain the title compound (white solid, 8.4 mg, 82%).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe concentration under reduced pressure
  7. washthe resulting solid was washed with dichloromethane

出典と根拠

ORDレコード
ord-4ba0df472d0d4106945d008cef41d0a6
出典データセット
uspto-grants-2015_09
特許番号
US09126931B2

反応ノート

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