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

HRID 746811

반응식

HRID 746811 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

Under argon, 25 mg copper iodide, 44 mg bis-(triphenylphosphine)-palladium dichloride, 0.30 ml triethylamine and finally 0.14 ml trimethylsilylacetylene are added 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 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 mixture is extracted three times with ethyl acetate, and the collected organic phases are dried over sodium sulphate. After the solvent has been eliminated 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 aqueous sodium chloride solution and extracted with ethyl acetate. The organic extracts collected are dried over sodium sulphate, and the solvent is removed. The residue is chromatographed 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 mixture is extracted three times with ethyl acetate
  4. dry with materialthe collected organic phases are dried over sodium sulphate
  5. dissolutionis dissolved in 5 ml of methanol
  6. stirringThe mixture is stirred for 1 h at ambient temperature
  7. customThen the methanol is evaporated off
  8. extractionextracted with ethyl acetate
  9. customThe organic extracts collected
  10. dry with materialare dried over sodium sulphate
  11. customthe solvent is removed
  12. customThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->5:1)

출처 및 근거

ORD 기록
ord-3d51829840d349e184d3c7ac4973081f
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393836B2

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