Réaction #1771996

Équation de réaction

dichloroacetic acid

Boc-norvalinol

toluene

EDC

→

Boc-norvalinal

Solvants

dimethylsulfoxide

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter addition
2. 2
   Températureto warm to room temperature over a period of 2 h
3. 3
   ConcentrationThe reaction mixture was concentrated
4. 4
   Autreto remove the toluene
5. 5
   workup.DISSOLUTIONdissolved in ethyl acetate
6. 6
   LavageThe solution was washed successively with 1N sodium bisulfate, saturated sodium bicarbonate and brine
7. 7
   Séchagedried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated

Mode opératoire

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 was washed successively with 1N 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).

Source