Triethylamine → 1-Chloro-2-(4-ethynyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

HRID 19827

反応式

HRID 19827 の反応式
C(N([CH2:6][CH3:7])CC)C.C[Si](C#C)(C)C.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C@:21]2([O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]2[OH:24])[OH:22])=[CH:17][C:16]=1[CH2:33][C:34]1[CH:39]=[CH:38][C:37](OS(C(F)(F)F)(=O)=O)=[CH:36][CH:35]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C@:21]2([O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]2[OH:24])[OH:22])=[CH:17][C:16]=1[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([C:6]#[CH:7])=[CH:38][CH:39]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 66111Trimethylsilylacetylene2 回HCID 516892Sodium BicarbonateHCID 866006751-chloro-4-(beta-D-glucopyranos-1-yl)-2-(4-trifluoromethylsulfonyloxy-benzyl)-benzene

生成物 1

HCID 866006811-Chloro-2-(4-ethynyl-benzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

25 mg of copper iodide, 44 mg of bis-(triphenylphosphine)-palladium dichloride, 0.30 ml triethylamine and finally 0.14 ml of trimethylsilylacetylene are added under argon to a solution of 0.32 g 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(trifluoromethylsulphonyloxy)-benzyl]-benzene in 3 ml of dimethylformamide. The flask is tightly sealed and the mixture is stirred for 8 h at 90° C. Then another 25 mg of bis-(triphenylphosphine)-palladium dichloride and 0.1 ml trimethylsilylacetylene are added, and the solution is stirred for a further 10 h at 90° C. Then aqueous sodium hydrogen carbonate solution is added, the resultant mixture is extracted three times with ethyl acetate, and the combined organic phases are dried over sodium sulfate. After the solvent has been evaporated, the residue is dissolved in 5 ml of methanol and combined with 0.12 g potassium carbonate. The mixture is stirred for 1 h at ambient temperature and then neutralised with 1 M hydrochloric acid. Then the methanol is evaporated off, the residue is combined with brine and extracted with ethyl acetate. The organic extracts collected are dried over sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1).

後処理

  1. customThe flask is tightly sealed
  2. stirringthe solution is stirred for a further 10 h at 90° C
  3. extractionthe resultant mixture is extracted three times with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. customAfter the solvent has been evaporated
  6. dissolutionthe residue is dissolved in 5 ml of methanol
  7. stirringThe mixture is stirred for 1 h at ambient temperature
  8. customThen the methanol is evaporated off
  9. extractionextracted with ethyl acetate
  10. customThe organic extracts collected
  11. dry with materialare dried over sodium sulfate
  12. customthe solvent is removed
  13. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1)

出典と根拠

ORDレコード
ord-b13a0167ff384e2e8d995c3b159b2e31
出典データセット
uspto-grants-2010_06
特許番号
US07745414B2

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