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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 2118165
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HRID 2118165 반응식
[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
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참가 물질

4

반응물 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

생성물 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-dimethylbenzenesulfonamide수율 61.7%

시약·촉매·용매 1

HCID 31268Pyrrolidine용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-f8b8b69fd2064558bdad60d3cf2088ef
출처 데이터셋
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07442836B2

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