Phosphate → N2-[(3-Iodophenyl)sulfonyl]-N2-{[2-(trimethylsilyl)ethoxy]methyl}glycinamide

HRID 2117687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2117687
[I:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH2:12][C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl.P([O-])([O-])([O-])=O>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]([CH2:23][O:22][CH2:21][CH2:20][Si:19]([CH3:26])([CH3:25])[CH3:18])[CH2:12][C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21895595N2-[(3-Iodophenyl)sulfonyl]glycinamide

Produkt 1

HCID 69197160N2-[(3-Iodophenyl)sulfonyl]-N2-{[2-(trimethylsilyl)ethoxy]methyl}glycinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N2-[(3-Iodophenyl)sulfonyl]glycinamide (0.14 g) was stirred with sodium hydride (60% oil dispersion, 0.02 g) in DMF (2 ml) at 21° under nitrogen for 15 min. 2-Trimethylsilylethoxymethyl chloride (0.08 ml) was added and stirring was continued for 1.5 h. The mixture was poured into pH 6.4 phosphate buffer and the product was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), concentrated and applied to a silica Bond Elut Cartridge (5 g) in dichloromethane containing methanol. The cartridge was eluted with dichloromethane, diethyl ether and ethyl acetate to give the title compound (0.16 g), LCMS RT=3.49 min.

Aufarbeitung

  1. extractionthe product was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additioncontaining methanol
  6. washThe cartridge was eluted with dichloromethane, diethyl ether and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3681a5a83aca4b69bbfb3367ede701d5
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442719B2

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