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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 503082Erstellt: 27. Oktober 2026

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

https://huagongshe.com/reaction/503082

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktPhosphateHCID 1061—
EduktSodium hydrideHCID 24758—
Eduktm-(Dimethylamino)benzyl alcoholHCID 90133—
Edukt2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonateHCID 46832228—
LösungsmittelDimethylformamideHCID 6228—
Produkt(5R)-3-[6-(2-{[3-(Dimethylamino)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 6684543195,2%

Reaktionsschritte

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 20° 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 20° 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.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07776895B2
Quelldatensatzuspto-grants-2010_08
ORD IDord-188e32319c374f3ab58a4cb48fe96801
Quellennotizuspto-grants-2010_08