Phosphate → (5R)-3-(6-bromohexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 219004Notes

Reaction equation

HRID 219004 reaction equation
[CH3:1][C:2]1([CH3:18])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[NH:14][CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.[H-].[Na+].P([O-])([O-])([O-])=O>CN(C=O)C.O>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:14]1[CH2:13][C@@H:12]([C:10]2[CH:9]=[CH:8][C:6]3[O:7][C:2]([CH3:18])([CH3:1])[O:3][CH2:4][C:5]=3[CH:11]=2)[O:16][C:15]1=[O:17]

Participants

7

Reactant 4

HCID 1061PhosphateHCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 66845427(5R)-3-(6-bromohexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (5.00 g) and 1,6-dibromohexane (9.26 ml) in DMF (50 ml) at 0° under nitrogen was treated in three equal portions with sodium hydride (60% dispersion in mineral oil, 963 mg). The mixture was stirred at 0° for 30 min and then at 20° for a further 2.5 h. Phosphate buffer solution (pH 6.5, 50 ml) and water (150 ml) were added and the mixture was extracted with diethyl ether (2×150 ml). The combined extracts were washed with water (2×150 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-dichloromethane (1:4) gave the title compound (7.10 g). LCMS RT=3.52 min, ES+ve 412 (MH)+, 414 (MH)+.

Workup

  1. waitat 20° for a further 2.5 h
  2. extractionthe mixture was extracted with diethyl ether (2×150 ml)
  3. washThe combined extracts were washed with water (2×150 ml)
  4. dry with materialwere dried (Na2SO4)
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel
  7. washElution with MeOH-dichloromethane (1:4)

Sources & evidence

ORD record
ord-0b19dcc3b7f24da59f1588d7e5d1c984
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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