Phosphate → 3-(Hydroxymethyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

HRID 219015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219015
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl.P([O-])([O-])([O-])=O>CN(C=O)C>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([S:9]([N:12]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])(=[O:10])=[O:11])[CH:6]=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 231337993-(Hydroxymethyl)benzene-1-sulfonamide

Produkt 1

HCID 468348293-(Hydroxymethyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-(hydroxymethyl)benzenesulfonamide (670 mg) in DMF (20 ml) under nitrogen was treated with sodium hydride (315 mg, 60% in oil) and the mixture was stirred at 20° for 15 min. The mixture was then treated with 2-(trimethylsilyl)ethoxymethyl chloride (1.27 ml) and the mixture was stirred at 20° for 1 h. Phosphate buffer solution (50 ml, pH6.5) was added and the mixture was extracted with EtOAc. The extract was washed with water, dried (Na2SO4) and the solvent evaporated in vacuo to give a residue. The residue was purified by chromatography on flash silica gel (40 mm diameter column). Elution with EtOAc-cyclohexane (3:7) gave the title compound (985 mg). LCMS RT=3.84 min.

Aufarbeitung

  1. stirringthe mixture was stirred at 20° for 1 h
  2. extractionthe mixture was extracted with EtOAc
  3. washThe extract was washed with water
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customto give a residue
  7. customThe residue was purified by chromatography on flash silica gel (40 mm diameter column)
  8. washElution with EtOAc-cyclohexane (3:7)

Quellen und Nachweise

ORD-Eintrag
ord-80fba331e0474a40843d2764738c87e2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198483B2

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