Phosphate → N-Cyclohexyl-3-{[2-(4-[2-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

HRID 916835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916835
[CH:1]1([N:7]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[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+].CS(O[CH2:34][CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][N:45]2[CH2:49][C@@H:48]([C:50]3[CH:61]=[CH:60][C:53]4[O:54][C:55]([CH3:59])([CH3:58])[O:56][CH2:57][C:52]=4[CH:51]=3)[O:47][C:46]2=[O:62])=[CH:39][CH:38]=1)(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C.O>[CH:1]1([N:7]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][CH2:34][CH2:35][O:36][C:37]3[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][N:45]4[CH2:49][C@@H:48]([C:50]5[CH:61]=[CH:60][C:53]6[O:54][C:55]([CH3:58])([CH3:59])[O:56][CH2:57][C:52]=6[CH:51]=5)[O:47][C:46]4=[O:62])=[CH:39][CH:38]=3)[CH:12]=2)(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

7

Edukt 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 66845530N-Cyclohexyl-3-(hydroxymethyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamideHCID 866016632-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethyl methanesulfonate

Produkt 1

HCID 69424487N-Cyclohexyl-3-{[2-(4-[2-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of N-cyclohexyl-3-(hydroxymethyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide (207 mg) in DMF (5 ml) under nitrogen was treated with sodium hydride (60% dispersion in mineral oil, 24 mg) and the mixture stirred at 20° C. for 15 min. A solution of 2-(4-{2-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethyl methanesulfonate [Example 15 i)] (170 mg) in DMF (3 ml) was added and the mixture stirred at 20° C. for 18 h. Phosphate buffer solution (pH 6.5, 15 ml) and water (15 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 “Flashmaster” chromatography on silica gel. Elution with EtOAc-cyclohexane (2:3) gave the title compound (125 mg). LCMS RT=4.35 min.

Aufarbeitung

  1. stirringthe mixture stirred at 20° C. for 18 h
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customSolvent evaporation in vacuo
  6. customgave a residue which
  7. customwas purified by “Flashmaster” chromatography on silica gel
  8. washElution with EtOAc-cyclohexane (2:3)

Quellen und Nachweise

ORD-Eintrag
ord-19717d1cd7ad41f7bdb9bae44e59dd09
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271197B2

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