1-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde → 2-(Tert-butyl-dimethyl-silanyl)-5-{[4-(tert-butyl-dimethyl-silanyloxy)-thiochroman-6-yl]-hydroxy-methyl}-imidazole-1-sulfonic acid dimethylamide

HRID 1174694ノート

反応式

HRID 1174694 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][CH:5]2[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[Li]CCCC.[CH3:25][N:26]([CH3:44])[S:27]([N:30]1[C:34]([CH:35]=[O:36])=[CH:33][N:32]=[C:31]1[Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])(=[O:29])=[O:28]>C1COCC1>[CH3:25][N:26]([CH3:44])[S:27]([N:30]1[C:34]([CH:35]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[S:8][CH2:7][CH2:6][CH:5]3[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[OH:36])=[CH:33][N:32]=[C:31]1[Si:37]([C:40]([CH3:42])([CH3:41])[CH3:43])([CH3:39])[CH3:38])(=[O:28])=[O:29]

参加物

5

反応物 3

HCID 99959681-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehydeHCID 59749549(6-Bromo-thiochroman-4-yl-oxy)-tert-butyl-dimethyl-silaneHCID 178418339Butyllithium

生成物 1

HCID 597495632-(Tert-butyl-dimethyl-silanyl)-5-{[4-(tert-butyl-dimethyl-silanyloxy)-thiochroman-6-yl]-hydroxy-methyl}-imidazole-1-sulfonic acid dimethylamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of (6-bromo-thiochroman-4-yl-oxy)-tert-butyl-dimethyl-silane (Intermediate-K3) (2.74 g, 7.64 mmol) in THF (30 mL) was treated with nBuLi (3.1 mL of a 2.5 M soln) at −78° C. for 30 m. A solution of 2-(tert-butyl-dimethyl-silanyl)-5-formyl-imidazole-1-sulfonic acid dimethylamide (see the General Method above, Intermediate K1) (2.42 g, 7.63 mmol) in THF (10 mL) was added via cannula. After 15 m, the reaction mixture was allowed to warm to rt for 16 h. The mixture was quenched with water, washed with brine and dried over Na2SO4. The solvent was removed and the residue was purified by chromatography on silica gel with 20% EtOAc:hexane to afford 2-(tert-butyl-dimethyl-silanyl)-5-{[4-(tert-butyl-dimethyl-silanyloxy)-thiochroman-6-yl]-hydroxy-methyl}-imidazole-1-sulfonic acid dimethylamide (Intermediate K4) as an oil, 4.12 g.

後処理

  1. additionwas added via cannula
  2. customThe mixture was quenched with water
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe residue was purified by chromatography on silica gel with 20% EtOAc

出典と根拠

ORDレコード
ord-cc711eefe37e4304aadb54de6f1d2c25
出典データセット
uspto-grants-2010_11
特許番号
US07838545B2

反応ノート

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