Hydrogen Peroxide → 4-(beta-D-glucopyranos-1-yl)-2-(4-methylsulfinyl-benzyl)-benzonitrile

HRID 19838

Reaction equation

HRID 19838 reaction equation
[OH:1]O.[OH:3][C@:4]1([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][CH:25]=3)[CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]>O.C(O)(C(F)(F)F)C(F)(F)F>[OH:3][C@:4]1([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([S:30]([CH3:31])=[O:1])=[CH:28][CH:29]=3)[CH:16]=2)[O:12][C@H:11]([CH2:13][OH:14])[C@@H:9]([OH:10])[C@H:7]([OH:8])[C@H:5]1[OH:6]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 866189584-(beta-D-glucopyranos-1-yl)-2-(4-methylsulfanyl-benzyl)-benzonitrile

Product 1

HCID 866189574-(beta-D-glucopyranos-1-yl)-2-(4-methylsulfinyl-benzyl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

35% Hydrogen peroxide in water (48 μL) is added to 4-(β-D-glucopyranos-1-yl)-2-(4-methylsulfanyl-benzyl)-benzonitrile (83 mg) in 1,1,1,3,3,3-hexafluoroisopropanol (2 mL). The resulting solution is stirred at ambient temperature for 1 h and then quenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution. The organic phase is separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->5:1).

Workup

  1. customquenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is removed
  6. customThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->5:1)

Sources & evidence

ORD record
ord-935f5aedee184cb99a23d3432b7a09be
Source dataset
uspto-grants-2010_06
Patent number
US07745414B2

Linked notes

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