Phosphate → (5R)-3-(6-{2-[(4-bromobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 219045Notes

Reaction equation

HRID 219045 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+].[Br:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1.P([O-])([O-])([O-])=O>CN(C=O)C.O>[Br:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:14]2[CH2:13][C@@H:12]([C:10]3[CH:9]=[CH:8][C:6]4[O:7][C:2]([CH3:28])([CH3:1])[O:3][CH2:4][C:5]=4[CH:11]=3)[O:16][C:15]2=[O:17])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 468319552-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(2-hydroxyethoxy)hexyl]-, (5R)-

Product 1

HCID 66845394(5R)-3-(6-{2-[(4-bromobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[(2-hydroxyethyl)oxy]hexyl}-1,3-oxazolidin-2-one (2.00 g) in DMF (25 ml) under nitrogen was treated with sodium hydride (244 mg, 60% in oil) and the mixture was stirred at 20° for 15 min. 4-Bromobenzyl bromide (1.40 g) was added and the mixture was stirred at 20° for 18 h. Phosphate buffer solution (50 ml, pH6.5) and water (50 ml) were added and the mixture was extracted with EtOAc. The extract was washed with water, dried (Na2SO4) and the solvent evaporated in vacuo to give a residue. The residue was purified by chromatography on flash silica gel (40 mm diameter column). Elution with EtOAc-PE (1:1) gave the title compound (2.125 g). LCMS RT=3.77 min.

Workup

  1. stirringthe mixture was stirred at 20° for 18 h
  2. extractionthe mixture was extracted with EtOAc
  3. washThe extract was washed with water
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customto give a residue
  7. customThe residue was purified by chromatography on flash silica gel (40 mm diameter column)
  8. washElution with EtOAc-PE (1:1)

Sources & evidence

ORD record
ord-205e08d8b0f347588890541c3fafb850
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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