반응 #1771996

반응 방정식

dichloroacetic acid

Boc-norvalinol

toluene

EDC

→

Boc-norvalinal

용매

dimethylsulfoxide

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   온도to warm to room temperature over a period of 2 h
3. 3
   농축The reaction mixture was concentrated
4. 4
   기타to remove the toluene
5. 5
   workup.DISSOLUTIONdissolved in ethyl acetate
6. 6
   세척The solution was washed successively with 1N sodium bisulfate, saturated sodium bicarbonate and brine
7. 7
   건조dried over sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated

실험 절차

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).

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