反应详情

温度

-20 °C

A suspension of ethyl-pyridin-2-ylmethyl-amine (29.0 mmol) and DIPEA (78.0 mmol) in DMF (50 mL) was cooled to −20° C. and added to a cold (−20° C.) solution of p-tolylamino-acetic acid (26.0 mmol) and TBTU (34.0 mmol) in DMF (100 mL). The reaction mixture was stirred for 15 min at −20° C. Water (300 mL) and ethyl acetate (400 mL) were added, the layers were separated and the organic layer washed with water (4×100 mL). The combined aqueous layers were extracted with ethyl acetate (200 mL). The combined organic layers were washed with NaOH solution (1.0 mol/L, 100 mL) and brine (100 mL) and dried with Na2SO4. The solvents were removed in vacuo and the obtained solid was dissolved in ethanol. By addition of a solution of hydrogen chloride in ether a byproduct precipitated which was filtered off. Dilution of the remaining solution with ether led to precipitation of the desired acetamide, which was obtained as a white solid (5.3 g).

1. customthe layers were separated
2. washthe organic layer washed with water (4×100 mL)
3. extractionThe combined aqueous layers were extracted with ethyl acetate (200 mL)
4. washThe combined organic layers were washed with NaOH solution (1.0 mol/L, 100 mL) and brine (100 mL)
5. dry with materialdried with Na2SO4
6. customThe solvents were removed in vacuo
7. dissolutionthe obtained solid was dissolved in ethanol
8. additionBy addition of a solution of hydrogen chloride in ether a byproduct
9. customprecipitated which
10. filtrationwas filtered off
11. customDilution of the remaining solution with ether led to precipitation of the desired acetamide