Phosphate → (5R)-3-[6-(2-([tert-butyl(dimethyl)silyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 218994

Reaktionsgleichung

Reaktionsgleichung von HRID 218994
[CH3:1][C:2]1([CH3:18])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[NH:14][CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[H-].[Na+].[CH3:21][SiH2:22][CH3:23].P([O-])([O-])([O-])=O.CN([CH:32]=[O:33])C>>[Si:22]([O:3][CH2:2][CH2:1][O:33][CH2:32][CH2:8][CH2:9][CH2:10][CH2:12][CH2:13][N:14]1[CH2:13][C@@H:12]([C:10]2[CH:9]=[CH:8][C:6]3[O:7][C:2]([CH3:18])([CH3:1])[O:3][CH2:4][C:5]=3[CH:11]=2)[O:16][C:15]1=[O:17])([C:5]([CH3:6])([CH3:4])[CH3:11])([CH3:23])[CH3:21]

Komponenten

6

Edukt 5

HCID 1061PhosphateHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 66185CID 66185HCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Produkt 1

HCID 46831954(5R)-3-[6-(2-([tert-butyl(dimethyl)silyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (0.83 g) in DMF (20 ml) was treated with sodium hydride (60% dispersion in mineral oil, 0.20 g) and the mixture stirred under nitrogen at 20° C. for 30 min. A solution of {2-[(6-bromohexyl)oxy]ethoxy}tert-butyl)dimethylsilane (1.47 g) in DMF (4 ml) was added and the mixture stirred at 20° C. for 90 min. Phosphate buffer (20 ml, pH6.5) was added, before partitioning between EtOAc (50 ml) and water (50 ml). The layers were separated and the aqueous layer re-extracted with EtOAc (3×30 ml). The combined organic layer was washed with water (3×50 ml) and dried over Na2SO4 before filtering. Solvent evaporation in vacuo gave a residue which was purified by flash chromatography on silica. Elution with EtOAc-cyclohexane (1:1) followed by solvent evaporation in vacuo gave the title compound (0.84 g). LCMS RT=4.11 min, ES+ve 507 (MH)+.

Aufarbeitung

  1. stirringthe mixture stirred at 20° C. for 90 min
  2. custombefore partitioning between EtOAc (50 ml) and water (50 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer re-extracted with EtOAc (3×30 ml)
  5. washThe combined organic layer was washed with water (3×50 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationbefore filtering
  8. customSolvent evaporation in vacuo
  9. customgave a residue which
  10. customwas purified by flash chromatography on silica
  11. washElution with EtOAc-cyclohexane (1:1)
  12. customfollowed by solvent evaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-35548232d13b47f29f7e03a154e52b60
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198483B2

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