Phosphate → N-Cyclohexyl-3-(hydroxymethyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

HRID 916834

Reaktionsgleichung

[CH:1]1([NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=2)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl.P([O-])([O-])([O-])=O>CN(C=O)C.O>[CH:1]1([N:7]([CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=2)(=[O:9])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

A solution of N-cyclohexyl-3-(hydroxymethyl)benzenesulfonamide (1.744 g) in DMF (30 ml) under nitrogen was treated with sodium hydride (60% dispersion in mineral oil, 311 mg) and the mixture stirred at 20° C. for 0.5 h. 2-(Trimethylsilyl)ethoxymethyl chloride (1.15 ml) was added and the mixture was stirred for a further 2 h at 20° C. Phosphate buffer solution (pH 6.5, 50 ml) and water (50 ml) were added and the mixture was extracted with EtOAc. The combined extracts were washed with water and dried (Na2SO4). Solvent evaporation in vacuo gave a residue which was purified by flash chromatography on silica gel. Elution with EtOAc-petroleum ether (3:7) gave the title compound (1.917 g). LCMS RT=3.83 min.

Aufarbeitung

stirringthe mixture was stirred for a further 2 h at 20° C
extractionthe mixture was extracted with EtOAc
washThe combined extracts were washed with water
dry with materialdried (Na2SO4)
customSolvent evaporation in vacuo
customgave a residue which
customwas purified by flash chromatography on silica gel
washElution with EtOAc-petroleum ether (3:7)

Quellen und Nachweise

ORD-Eintrag: ord-284d08244fb64db1b6596ddf37836815
Quelldatensatz: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07271197B2

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