反应详情

温度

0 °C

To Boc-norvalinol (7.77 g, 38 mmol), in anhydrous dimethylsulfoxide (153 mL) and toluene (153 mL) was added EDC (73.32 g, 382 mmol). After the solution was cooled to 0° C., dichloroacetic acid (15.8 mL, 191 mmol) was added dropwise. After addition was complete, the reaction was stirred for 15 min. The solution was allowed to warm to room temperature over a period of 2 h. The reaction mixture was concentrated to remove the toluene, then dissolved in ethyl acetate. The solution washed successively with 1 N sodium bisulfate, saturated sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated to afford crude Boc-norvalinal which was used directly in the next step. TLC Rf=0.84 (40% ethyl acetate/hexanes).

1. additionAfter addition
2. temperatureto warm to room temperature over a period of 2 h
3. concentrationThe reaction mixture was concentrated
4. customto remove the toluene
5. dissolutiondissolved in ethyl acetate
6. washThe solution washed successively with 1 N sodium bisulfate, saturated sodium bicarbonate and brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated