Phosphate → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[2-{(3-nitrophenyl)-methoxy}ethoxy]hexyl}-1,3-oxazolidin-2-one

HRID 218996Notes

Reaction equation

HRID 218996 reaction equation
[CH3:1][C:2]1([CH3:28])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27])[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[H-].[Na+].[N+:31]([C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37]Br)([O-:33])=[O:32].P([O-])([O-])([O-])=O>CN(C=O)C>[CH3:1][C:2]1([CH3:28])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:37][C:36]4[CH:39]=[CH:40][CH:41]=[C:34]([N+:31]([O-:33])=[O:32])[CH:35]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 468319552-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(2-hydroxyethoxy)hexyl]-, (5R)-

Product 1

HCID 46833387(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[2-{(3-nitrophenyl)-methoxy}ethoxy]hexyl}-1,3-oxazolidin-2-oneYield 37.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(2-hydroxyethoxy)hexyl]-1,3-oxazolidin-2-one (0.20 g) in DMF (5 ml) was treated with sodium hydride (60% dispersion in mineral oil, 0.030 g) and the mixture stirred under nitrogen at 20° C. for 15 min. 3-nitrobenzylbromide (0.11 g) was added, and the mixture stirred at 20° C. for a further 3 h. Phosphate buffer (20 ml, pH6.5) was added and the mixture was stirred for 5 min before extracting with EtOAc (3×20 ml). The organic layer was washed with water (3×20 ml), dried over Na2SO4 and filtered. Solvent evaporation gave the crude product which was purified by flash chromatography on silica. Elution with EtOAc-cyclohexane (7:3) followed by solvent evaporation in vacuo gave the title compound (0.10 g). LCMS RT=3.61 min, ES+ve 529 (MH)+.

Workup

  1. stirringthe mixture stirred at 20° C. for a further 3 h
  2. stirringthe mixture was stirred for 5 min
  3. extractionbefore extracting with EtOAc (3×20 ml)
  4. washThe organic layer was washed with water (3×20 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customSolvent evaporation
  8. customgave the crude product which
  9. customwas purified by flash chromatography on silica
  10. washElution with EtOAc-cyclohexane (7:3)
  11. customfollowed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-9e548afe66ae4890866adca37fc0114c
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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