Water → tert-butyl 4-(2-(2-(2-(4-((4-iodophenoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethoxy)phenylcarbamate

HRID 333136ノート

反応式

HRID 333136 の反応式
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:15][CH:14]=1)=[N+:2]=[N-:3].[I:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]#[CH:37])=[CH:30][CH:29]=1.O>C1COCC1.[O-]S([O-])(=O)=O.[Cu+2]>[I:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]2[N:3]=[N:2][N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[CH:17][CH:18]=3)[CH:37]=2)=[CH:30][CH:29]=1

参加物

6

反応物 3

HCID 962WaterHCID 138392501-Iodo-4-(prop-2-yn-1-yloxy)benzeneHCID 57773644Tert-butyl 4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenylcarbamate

生成物 1

HCID 57773633tert-butyl 4-(2-(2-(2-(4-((4-iodophenoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethoxy)phenylcarbamate収率 68.2%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenylcarbamate (1.78 g, 4.86 mmol) and 1-iodo-4-(prop-2-ynyloxy)benzene (1.25 g, 4.86 mmol) in THF (30 mL) was added H2O (8.0 mL), Cu powder (0.31 g, 4.86 mmol) and CuSO4 (0.12 g, 0.486 mmol). The reaction mixture was stirred at room temperature for at least 12 hours (overnight). The reaction mixture was filtered through celite and washed with EtOAc. The organic layer was separated, washed with EDTA solution, dried and concentrated in vacuo to give a crude product which was purified by flash chromatography with hexane/EtOAc (1:1) as eluent to give tert-butyl 4-(2-(2-(2-(4-((4-iodophenoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethoxy)phenylcarbamate (2.069 g, 68%). 1H NMR (400 MHz, CDCl3) δ 7.74 (s, 1H), 7.46 (d, J=9.2 Hz, 2H), 7.15 (d, J=8.8 Hz, 2H), 6.74 (d, J=9.2 Hz, 2H), 6.66 (d, J=8.8 Hz, 2H), 6.25 (brs, 1H), 5.04 (s, 2H), 4.47 (t, J=5.0 Hz, 2H), 3.99 (t, J=4.8 Hz, 2H), 3.79 (t, J=5.0 Hz, 2H), 3.80 (t, J=5.0 Hz, 2H), 3.71 (t, J=5.0 Hz, 2H), 3.60-3.53 (m, 4H), 1.44 (s, 9H); MS (ESI), 625 (M+H)+.

後処理

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with EtOAc
  3. customThe organic layer was separated
  4. washwashed with EDTA solution
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. customwas purified by flash chromatography with hexane/EtOAc (1:1) as eluent

出典と根拠

ORDレコード
ord-c11feed6b8864862892ae499a19d6c45
出典データセット
uspto-grants-2014_11
特許番号
US08877970B2

反応ノート

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