2-(2-(2-Azidoethoxy)ethoxy)ethanol → Mono-2-(2-(2-(4-(methylene)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethanol-curcumin

HRID 452022Notes

Reaction equation

HRID 452022 reaction equation
C([CH:4]([C:18](/[CH:20]=[CH:21]/[C:22]1[CH:30]=[C:27]([O:28][CH3:29])[C:25]([OH:26])=[CH:24][CH:23]=1)=[O:19])[C:5](=[O:17])/[CH:6]=[CH:7]/[C:8]1[CH:9]=[C:10]([C:13]([OH:16])=[CH:14][CH:15]=1)[O:11][CH3:12])C#C.[N:31]([CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])=[N+:32]=[N-:33].O=[C:44]1O[C@H]([C@H](CO)O)[C:47]([O-])=[C:45]1O.[Na+]>CC(O)(C)C.C(Cl)(Cl)Cl.O.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:29][O:28][C:27]1[C:25]([OH:26])=[CH:24][CH:23]=[C:22](/[CH:21]=[CH:20]/[C:18]([CH2:4][C:5](/[CH:6]=[CH:7]/[C:8]2[CH:9]=[C:10]([O:11][CH3:12])[C:13]([OH:16])=[CH:14][CH:15]=2)=[O:17])=[O:19])[CH:30]=1.[CH2:44]=[C:45]1[CH2:47][N:31]([CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])[N:32]=[N:33]1

Participants

8

Reactant 3

HCID 110084382-(2-(2-Azidoethoxy)ethoxy)ethanolHCID 23667548Sodium AscorbateHCID 88539422Mono-Propargyl Curcumin

Product 1

HCID 131730719Mono-2-(2-(2-(4-(methylene)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethanol-curcuminYield 26%

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of Mono-Propargyl Curcumin 5 (63 mg, 0.16 mmol) and 2-(2-(2-azidoethoxy)ethoxy)ethanol (46 mg, 0.26 mmol) in tBuOH (1.1 mL) and CHCl3 (0.3 mL) was added a prepared solution of Cu(OAc)2 (8 mg, 0.03 mmol) and sodium ascorbate (13 mg, 0.07 mmol) in H2O (1.3 mL). After vigorous stirring overnight the solvent was removed under vacuum. The mixture was dissolved in CHCl3, washed with H2O and the organic phase was separated, dried over Na2SO4 and evaporated. Purification was performed by column chromatography, eluting with CH2Cl2-CH2Cl2: MeOH 98:2. Yield 26%. NMR NMR 1H (CDCl3), δ (ppm): 3.55-3.60 (m, 8H); 3.72-3.72 (t, 3H); 3.87-3.94 (m, 8H); 4.54-4.55 (t, 2H); 5.80 (s, 1H); 6.07 (s, 1H); 6.46-6.50 (dd, 2H); 6.92-6.94 (d, 1H); 7.05-7.12 (m, 5H); 7.56-7.60 (q, 2H); 7.92 (s, 1H).). MS (ESI) calcd. for C30H35N3O9: 581.61. Found: 582.3 [M+H]+, 604.3 [M++Na], 620.3 [M++K].

Workup

  1. customwas removed under vacuum
  2. dissolutionThe mixture was dissolved in CHCl3
  3. washwashed with H2O
  4. customthe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customPurification
  8. washeluting with CH2Cl2-CH2Cl2

Sources & evidence

ORD record
ord-b47b36a534c54e639febfd0283672cb1
Source dataset
uspto-grants-2013_07
Patent number
US08487139B2

Reaction notes

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