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Tetrabutylammonium Fluoride → N-{[4-(hydroxymethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide

HRID 607427
ノート
印刷プレビュー

反応式

HRID 607427 の反応式
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:44])(=[O:43])=[N:17][C:18](=[O:42])[C:19]2[CH:24]=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]4[O:37][CH:38]=[CH:39][C:40]=4[CH3:41])=[O:35])[CH:28]=3)[CH:22]=[N:21][CH:20]=2)=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:44])(=[O:43])=[N:17][C:18](=[O:42])[C:19]2[CH:24]=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]4[O:37][CH:38]=[CH:39][C:40]=4[CH3:41])=[O:35])[CH:28]=3)[CH:22]=[N:21][CH:20]=2)=[CH:12][CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 57657965N-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl](methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide

生成物 1

HCID 57657893N-{[4-(hydroxymethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide収率 94%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran
溶媒
2 回
HCID 8857Ethyl Acetate溶媒

実験手順

N-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl](methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)nicotinamide (0.722 g, 1.15 mmol) was dissolved in THF (2.3 mL). The resulting solution was treated with 1M solution of TBAF in THF (2.3 mL, 2.30 mmol) causing the mixture to turn black in color. The mixture was allowed to stir for 1 h, subsequently dissolved in EtOAc (10 mL) and extracted with H2O (3×15 mL). The organic layer was dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude product was purified via column chromatography (gradient eluant mixture of EtOAc in Hexanes: 0% to 100% EtOAc) to afford the title compound in 94% yield (0.350 g, 0.682 mmol).

後処理

  1. extractionextracted with H2O (3×15 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4(s)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified via column chromatography (gradient eluant mixture of EtOAc in Hexanes: 0% to 100% EtOAc)

出典と根拠

ORDレコード
ord-eeee594599414b9285630070c5275b2b
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07915443B2

反応ノート

読み込み中…

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