3-bromo-N,N-dimethylbenzenesulfonamide → 3-[4-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)but-1-ynyl]-N,N-dimethylbenzenesulfonamide

HRID 2118165Notes

Reaction equation

HRID 2118165 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:16][C@@H:15]([C:17]2[CH:28]=[CH:27][C:20]3[O:21][C:22]([CH3:26])([CH3:25])[O:23][CH2:24][C:19]=3[CH:18]=2)[O:14][C:13]1=[O:29])[CH2:2][C:3]#[CH:4].Br[C:31]1[CH:32]=[C:33]([S:37]([N:40]([CH3:42])[CH3:41])(=[O:39])=[O:38])[CH:34]=[CH:35][CH:36]=1>N1CCCC1>[CH3:26][C:22]1([CH3:25])[O:21][C:20]2[CH:27]=[CH:28][C:17]([C@H:15]3[O:14][C:13](=[O:29])[N:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:1][CH2:2][C:3]#[C:4][C:35]4[CH:34]=[C:33]([S:37]([N:40]([CH3:42])[CH3:41])(=[O:38])=[O:39])[CH:32]=[CH:31][CH:36]=4)[CH2:16]3)=[CH:18][C:19]=2[CH2:24][O:23]1

Participants

4

Reactant 2

HCID 71298453-bromo-N,N-dimethylbenzenesulfonamideHCID 42625666(5R)-3-[6-(But-3-ynyloxy)hexyl]5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 426251673-[4-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)but-1-ynyl]-N,N-dimethylbenzenesulfonamideYield 61.7%

Reagents, catalysts & solvents 1

HCID 31268PyrrolidineSolvent

Procedure

A mixture of (5R)-3-[6-(but-3-ynyloxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (0.256 g) and 3-bromo-N,N-dimethylbenzene sulphonamide (0.208 g) in pyrrolidine (4 ml) was degassed using vacuum/nitrogen cycle. Cuprous iodide (0.005 g) and dichlorobis(triphenylphosphine)palladium (0.037 g) were added and the mixture was stirred at 80° for 45 min under nitrogen. The mixture was diluted with EtOAc and washed with water. The aqueous phase was extracted with EtOAc and the combined organic phases washed with brine, dried (Na2SO4) and evaporated to dryness. The residue was dissolved in CH2Cl2 and applied to a silica Bond Elut Cartridge (10 g). The cartridge was eluted with CH2Cl2, cyclohexane/Et2O, Et2O and EtOAc. Evaporation of the ether fractions gave an oil which was repurified by silica Bond Elut to give the title compound (0.23 g), ES+ve 585 (MH)+.

Workup

  1. customwas degassed
  2. additionCuprous iodide (0.005 g) and dichlorobis(triphenylphosphine)palladium (0.037 g) were added
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with water
  5. extractionThe aqueous phase was extracted with EtOAc
  6. washthe combined organic phases washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated to dryness
  9. dissolutionThe residue was dissolved in CH2Cl2
  10. washThe cartridge was eluted with CH2Cl2, cyclohexane/Et2O, Et2O and EtOAc
  11. customEvaporation of the ether fractions
  12. customgave an oil which
  13. customwas repurified by silica Bond Elut

Sources & evidence

ORD record
ord-f8b8b69fd2064558bdad60d3cf2088ef
Source dataset
uspto-grants-2008_10
Patent number
US07442836B2

Reaction notes

Loading…