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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 2118280
ノート
印刷プレビュー

反応式

HRID 2118280 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 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-dimethylbenzenesulfonamide収率 61.7%

試薬・触媒・溶媒 1

HCID 31268Pyrrolidine溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-07ae7239fc9b4017a151d6be0e5087ca
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07442837B2

反応ノート

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