Phosphate → (5R)-3-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 219006Notes

Reaction equation

HRID 219006 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+].[Cl:31][C:32]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:33]=1[CH2:34]Br.P([O-])([O-])([O-])=O>CN(C=O)C>[Cl:31][C:32]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:33]=1[CH2:34][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:14]1[CH2:13][C@@H:12]([C:10]2[CH:9]=[CH:8][C:6]3[O:7][C:2]([CH3:28])([CH3:1])[O:3][CH2:4][C:5]=3[CH:11]=2)[O:16][C:15]1=[O:17]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 468319552-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(2-hydroxyethoxy)hexyl]-, (5R)-

Product 1

HCID 46833391(5R)-3-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (200 mg) in DMF (4 ml) under nitrogen was treated with sodium hydride (26 mg, 60% in oil) and the mixture was stirred at 20° for 10 min. 2,6-Dichlorobenzyl bromide (122 mg) was added and the mixture was stirred at 20° for 3 h. Phosphate buffer solution (20 ml, pH6.5) was added and the mixture was extracted with EtOAc (30 ml). The extract was washed with water (2×20 ml), dried (NaSO4) and the solvent evaporated in vacuo to give a residue. The residue was purified by chromatography on flash silica gel 20 mm diameter column. Elution with EtOAc-cyclohexane (1:1) gave the title compound (155 mg). LCMS RT=3.97 min.

Workup

  1. stirringthe mixture was stirred at 20° for 3 h
  2. extractionthe mixture was extracted with EtOAc (30 ml)
  3. washThe extract was washed with water (2×20 ml)
  4. dry with materialdried (NaSO4)
  5. customthe solvent evaporated in vacuo
  6. customto give a residue
  7. customThe residue was purified by chromatography on flash silica gel 20 mm diameter column
  8. washElution with EtOAc-cyclohexane (1:1)

Sources & evidence

ORD record
ord-421fc2be2ba94d81942059bb00a6b970
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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