反応 #535366

反応方程式

ferulic acid

triethylamine

3-hydroxytyramine

→

N-trans-feruloyldopamine

溶媒

dichloromethane

DMF

反応条件

後処理

1. 1
   その他the dichloromethane is evaporated off under vacuum
2. 2
   workup.ADDITION30 mL of water are added to the remaining solution
3. 3
   その他the mixture obtained
4. 4
   抽出is extracted with ethyl acetate (3×75 mL)
5. 5
   洗浄The organic phase is successively washed with 100 mL of 1N HCl solution, 100 mL of water and 100 mL of 1M sodium bicarbonate (NaHCO3) solution
6. 6
   乾燥It is then dried over sodium sulfate
7. 7
   その他evaporated to dryness
8. 8
   その他The product obtained

実験手順

A solution of ferulic acid (300 mg; 1.54 mmol) and of triethylamine (1.5 eq; 2.31 mmol) in DMF (3.5 mL) is cooled to 3 or 4° C. using an ice bath. An amine, 3-hydroxytyramine (dopamine) (1 eq; 1.54 mmol) is added to the medium, followed by addition of a solution of BOP (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; (1 eq; 1.54 mmol) in dichloromethane (3.5 mL); the mixture is stirred for about thirty minutes in the ice bath and then for 20 hours at room temperature. Stirring is then stopped and the dichloromethane is evaporated off under vacuum. 30 mL of water are added to the remaining solution and the mixture obtained is extracted with ethyl acetate (3×75 mL). The organic phase is successively washed with 100 mL of 1N HCl solution, 100 mL of water and 100 mL of 1M sodium bicarbonate (NaHCO3) solution. It is then dried over sodium sulfate and evaporated to dryness. The product obtained is in the form of a white precipitate after chromatography on a column of silica gel.

出典