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

HRID 2118312
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2118312
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

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 6228
Dimethylformamide
Lösungsmittel

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-9157c2441c4f4a9faa51055c11776a80
Quelldatensatz
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07442837B2

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