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N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2) → (E)-[2-(3-{4-[1-(4-Bromo-phenylcarbamoyl)-3-hydroxy-propyl]phenyl}-acryloylamino)-phenyl]carbamic acid tert-butyl ester

HRID 220174
ノート
印刷プレビュー

反応式

HRID 220174 の反応式
[C:1]([O:5][C:6](=[O:46])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:45])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:35](=[O:44])[NH:36][C:37]2[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=2)[CH2:25][CH2:26][O:27][Si](C(C)(C)C)(C)C)=[CH:20][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.F.F.[F-]>C1COCC1>[C:1]([O:5][C:6](=[O:46])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:45])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:35](=[O:44])[NH:36][C:37]2[CH:38]=[CH:39][C:40]([Br:43])=[CH:41][CH:42]=2)[CH2:25][CH2:26][OH:27])=[CH:20][CH:19]=1)([CH3:4])([CH3:2])[CH3:3]
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 11748636N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2)HCID 59238282(E)-[2-(3-{4-[1-(4-Bromo-phenylcarbamoyl)-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester

生成物 1

HCID 59238323(E)-[2-(3-{4-[1-(4-Bromo-phenylcarbamoyl)-3-hydroxy-propyl]phenyl}-acryloylamino)-phenyl]carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of (E)-[2-(3-{4-[1-(4-bromo-phenylcarbamoyl)-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (1.6 g, 2.26 mmol) in THF (40 mL) was added tetrabutylammonium dihydrogen trifluoride (1.36 g, 4.52 mmol). This mixture was stirred at room temperature overnight and then evaporated to remove THF. The mixture was dissolved in water and extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated. The crude product was purified by column chromatography (CH2Cl2:EtOAc=10:1) to get yellow solid product. MS: calc'd 594 (MH+), exp 594 (MH+).

後処理

  1. customevaporated
  2. customto remove THF
  3. dissolutionThe mixture was dissolved in water
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by column chromatography (CH2Cl2:EtOAc=10:1)
  10. customto get yellow solid product

出典と根拠

ORDレコード
ord-b32e868c6d2b43aea803d8f3db5e32f9
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202866B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート