Sodium Bicarbonate → 4-(beta-D-glucopyranos-1-yl)-2-(4-pentafluoroethyl-benzyl)-benzonitrile

HRID 502861노트

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HRID 502861 반응식
C([O:4][C@@H:5]1[C@@H:11]([O:12]C(=O)C)[C@H:10]([O:16]C(=O)C)[C@@H:9]([CH2:20][O:21]C(=O)C)[O:8][C@@:6]1([C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([CH2:33][C:34]2[CH:39]=[CH:38][C:37](I)=[CH:36][CH:35]=2)[CH:26]=1)[OH:7])(=O)C.[F:41][C:42]([Si](C)(C)C)([F:47])[C:43]([F:46])([F:45])[F:44].[F-].[K+].C([O-])(O)=O.[Na+]>[Cu]I.CN(C=O)C>[OH:7][C@:6]1([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([C:42]([F:47])([F:41])[C:43]([F:46])([F:45])[F:44])=[CH:36][CH:35]=3)[CH:26]=2)[O:8][C@H:9]([CH2:20][OH:21])[C@@H:10]([OH:16])[C@H:11]([OH:12])[C@H:5]1[OH:4]

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 522689Potassium FluorideHCID 2760820(Pentafluoroethyl)trimethylsilaneHCID 866162504-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile

생성물 1

HCID 866162494-(beta-D-glucopyranos-1-yl)-2-(4-pentafluoroethyl-benzyl)-benzonitrile

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A flask charged with 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile (0.16 g), pentafluoroethyltrimethylsilane (0.14 g), KF (43 mg), CuI (0.16 g), DMF (2 mL) and Ar atmosphere is heated at 60° C. for 24 h. Then, aqueous NaHCO3 solution is added and the resulting mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is dissolved in methanol (8 mL) and treated with 4 M KOH solution (0.8 mL). The solution is stirred at room temperature for 1 h and then diluted with aqueous NaHCO3 solution. After removal of the methanol under reduced pressure, the residue is extracted with ethyl acetate, the combined organic extracts are dried and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1).

후처리

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. customthe solvent is removed
  4. dissolutionThe residue is dissolved in methanol (8 mL)
  5. additiontreated with 4 M KOH solution (0.8 mL)
  6. additiondiluted with aqueous NaHCO3 solution
  7. customAfter removal of the methanol under reduced pressure
  8. extractionthe residue is extracted with ethyl acetate
  9. customthe combined organic extracts are dried
  10. customthe solvent is removed
  11. customThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1)

출처 및 근거

ORD 기록
ord-4702331ee8d9449e95684ad0435736f6
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776830B2

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