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

HRID 333136Notes

Reaction equation

HRID 333136 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-c11feed6b8864862892ae499a19d6c45
Source dataset
uspto-grants-2014_11
Patent number
US08877970B2

Reaction notes

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