Iodine chloride → 4-(beta-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile

HRID 1041944

Reaktionsgleichung

Reaktionsgleichung von HRID 1041944
[I:1]Cl.[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]([Si](C)(C)C)=[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]>ClCCl>[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]([I:1])=[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]

Komponenten

4

Edukt 2

HCID 24640Iodine chlorideHCID 866162484-(beta-D-glucopyranos-1-yl)-2-(4-trimethylsilyl-benzyl)-benzonitrile

Produkt 1

HCID 866162474-(beta-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 1 M solution of iodine monochloride in dichloromethane (0.9 mL) is added to 4-(β-D-glucopyranos-1-yl)-2-(4-trimethylsilyl-benzyl)-benzonitrile (0.26 g) dissolved in dichloromethane (5 mL). The solution is stirred at room 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->8:1).

Aufarbeitung

  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->8:1)

Quellen und Nachweise

ORD-Eintrag
ord-e597a9c802674a4a9dc3c6190c622dcb
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557782B2

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