反应详情

温度

60 °C

N-butyl-N-(2,3-dimethoxybenzyl)-3-(4-hydroxyphenyl)propanamide (50 mg, 0.13 mmol) and methyl 2-(bromomethyl)benzoate (0.034 g, 0.15 mmol) was dissolved in acetonitrile (10 ml) and potassium carbonate (37 mg, 0.27 mmol) was added. The mixture was stirred at 60° C. for three hours. Polymer supported trisamine (0.3 eqv) was added and stirred overnight. The polymer was filtered off and solvent was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with three portions of water. After drying the crude (MgSO4), the solvent had been removed by evaporation. The residue was purified by preparative HPLC (started with acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). Removing the solvent by evaporation gave 15 mg of methyl 2-[(4-{3-[butyl(2,3-dimethoxybenzyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate (21.4%).

1. additionwas added
2. stirringstirred overnight
3. filtrationThe polymer was filtered off
4. customsolvent was removed by evaporation
5. additionEtOAc (10 ml) was added
6. washthe organic phase was washed with three portions of water
7. dry with materialAfter drying the crude (MgSO4)
8. customthe solvent had been removed by evaporation
9. customThe residue was purified by preparative HPLC (
10. concentrationthe acetonitrile concentration
11. temperaturewas increased to 100%
12. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)
13. additionThe product containing fractions
14. customthe acetonitrile was removed by evaporation
15. additionEtOAc (10 ml) was added
16. washthe organic phase was washed with two portions of brine
17. dry with materialdried (MgSO4)
18. customRemoving the solvent
19. customby evaporation