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

HRID 19838

반응식

HRID 19838 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 135291,1,1,3,3,3-Hexafluoro-2-propanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-935f5aedee184cb99a23d3432b7a09be
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745414B2

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