Ethylene Glycol → 2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(2-hydroxyethoxy)hexyl]-, (5R)-

HRID 219005Notes

Reaction equation

HRID 219005 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:18][C@@H:17]([C:19]2[CH:30]=[CH:29][C:22]3[O:23][C:24]([CH3:28])([CH3:27])[O:25][CH2:26][C:21]=3[CH:20]=2)[O:16][C:15]1=[O:31].P([O-])([O-])([O-])=O>CN(C=O)C.O>[CH3:27][C:24]1([CH3:28])[O:23][C:22]2[CH:29]=[CH:30][C:19]([C@H:17]3[O:16][C:15](=[O:31])[N:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:3][CH2:2][CH2:1][OH:4])[CH2:18]3)=[CH:20][C:21]=2[CH2:26][O:25]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 1061PhosphateHCID 24758Sodium hydrideHCID 66845427(5R)-3-(6-bromohexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 468319552-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(2-hydroxyethoxy)hexyl]-, (5R)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethylene glycol (5.00 ml) in DMF (40 ml) under nitrogen at 0° was treated portionwise with sodium hydride (60% dispersion in mineral oil, 1.292 g) and the mixture was stirred at 0° for 15 min. A solution of (5R)-3-(6-bromohexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (7.40 g) in DMF (10 ml) was added. The mixture was stirred at 0° for 0.5 h then at 20° for 3 h. Phosphate buffer solution (pH 6.5, 40 ml) and water (160 ml) were added and the mixture was extracted with EtOAc (2×100 ml). The combined extracts were washed with water (2×150 ml), brine (50 ml) and were dried (Na2SO4). The solvent was evaporated in vacuo and the residue was purified by flash chromatography on silica gel. Elution with MeOH-EtOAc (1:9) gave the title compound (4.10 g). LCMS RT=2.90 min, ES+ve 394 (MH)+.

Workup

  1. stirringThe mixture was stirred at 0° for 0.5 h
  2. waitat 20° for 3 h
  3. extractionthe mixture was extracted with EtOAc (2×100 ml)
  4. washThe combined extracts were washed with water (2×150 ml), brine (50 ml)
  5. dry with materialwere dried (Na2SO4)
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by flash chromatography on silica gel
  8. washElution with MeOH-EtOAc (1:9)

Sources & evidence

ORD record
ord-c25028c9740f45c69585121c42df696b
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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