반응 #42346

반응 방정식

Boc-L-alanine

isobutylamine

diisopropylethylamine

HOBt

→

title compound

N1-Isobutyl-L-alaninamide

용매

ethyl acetate

EDC

DMF

반응 조건

후처리

1. 1
   세척washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
2. 2
   건조dried (magnesium sulfate)
3. 3
   여과filtered
4. 4
   농축concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue is redissolved in 4N hydrochloric acid in dioxane (30 mL)
6. 6
   workup.STIRRINGstirred for 2 h
7. 7
   농축The solution is concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONdissolved in chloroform
9. 9
   세척washed with 1 N NaOH (aq)
10. 10
    추출The aqueous layer is extracted with chloroform
11. 11
    건조the pooled organics are dried (sodium sulfate)
12. 12
    여과filtered
13. 13
    농축concentrated under reduced pressure

실험 절차

Boc-L-alanine (5.0 g, 26.4 mmol), isobutylamine (2.9 mL, 29.1 mmol), diisopropylethylamine (11.5 mL, 66 mmol), and HOBt (3.6 g, 26.4 mmol) in anhydrous DMF (15 mL) is stirred 15 min. EDC is added, and the reaction is stirred at room temperature 16 h. The reaction is diluted in ethyl acetate and washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The residue is redissolved in 4N hydrochloric acid in dioxane (30 mL) and stirred for 2 h. The solution is concentrated under reduced pressure, dissolved in chloroform and washed with 1 N NaOH (aq). The aqueous layer is extracted with chloroform, and the pooled organics are dried (sodium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 145.2 [M+H]+.

출처