Reacción #90866

Ecuación de reacción

Mono-Propargyl Curcumin

2-(2-(2-azidoethoxy)ethoxy)ethanol

sodium ascorbate

→

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

Rendimiento 26.0%

Disolventes

tBuOH

CHCl3

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas removed under vacuum
2. 2
   workup.DISSOLUTIONThe mixture was dissolved in CHCl3
3. 3
   Lavadowashed with H2O
4. 4
   Otrothe organic phase was separated
5. 5
   Secadodried over Na2SO4
6. 6
   Otroevaporated
7. 7
   OtroPurification
8. 8
   Lavadoeluting with CH2Cl2—CH2Cl2

Procedimiento

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 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].

Fuente