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

HRID 19837Notes

Reaction equation

HRID 19837 reaction equation
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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-0cd75b91bc7e4e79a12351d6e22cd762
Source dataset
uspto-grants-2010_06
Patent number
US07745414B2

Reaction notes

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