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

HRID 1041938

반응식

HRID 1041938 반응식
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

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 66111Trimethylsilylacetylene2회HCID 516892Sodium BicarbonateHCID 866006751-chloro-4-(beta-D-glucopyranos-1-yl)-2-(4-trifluoromethylsulfonyloxy-benzyl)-benzene

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매2회HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1889e3c0912446aeaae81ef778a9ba96
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557782B2

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