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

HRID 901620

Reaktionsgleichung

Reaktionsgleichung von HRID 901620
[CH3:1][N:2]([CH3:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[H-].[Na+].CS(O[CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:32][C@@H:31]([C:33]2[CH:44]=[CH:43][C:36]3[O:37][C:38]([CH3:42])([CH3:41])[O:39][CH2:40][C:35]=3[CH:34]=2)[O:30][C:29]1=[O:45])(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C>[CH3:1][N:2]([CH3:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][O:7][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:32][C@@H:31]([C:33]2[CH:44]=[CH:43][C:36]3[O:37][C:38]([CH3:41])([CH3:42])[O:39][CH2:40][C:35]=3[CH:34]=2)[O:30][C:29]1=[O:45]

Komponenten

6

Edukt 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 90133m-(Dimethylamino)benzyl alcoholHCID 468322282-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonate

Produkt 1

HCID 66845431(5R)-3-[6-(2-{[3-(Dimethylamino)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 3-dimethylaminobenzyl alcohol (641 mg) in DMF (3 ml) under nitrogen was treated with sodium hydride (220 mg, 60% in oil) and the mixture stirred at 200 for 15 min. A solution of 2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonate (2.00 g) in DMF (5 ml) was added and the mixture was stirred at 200 for 21 h. Phosphate buffer solution (15 ml, pH6.5) was added, the mixture stirred for 15 min and then extracted with EtOAc. The combined organic layers were washed with water, dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by Biotage (40 g). Elution with EtOAc-PE (1:2) gave the title compound (2.125 g). LCMS RT=3.47 min.

Aufarbeitung

  1. stirringthe mixture was stirred at 200 for 21 h
  2. stirringthe mixture stirred for 15 min
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by Biotage (40 g)
  8. washElution with EtOAc-PE (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-426eda481d6b4994804e5822bf57289d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361787B2

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