Reaktion #42346

Reaktionsgleichung

Boc-L-alanine

isobutylamine

diisopropylethylamine

HOBt

→

title compound

N1-Isobutyl-L-alaninamide

Lösungsmittel

ethyl acetate

EDC

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
2. 2
   Trocknendried (magnesium sulfate)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated 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
   EinengenThe solution is concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONdissolved in chloroform
9. 9
   Waschenwashed with 1 N NaOH (aq)
10. 10
    ExtraktionThe aqueous layer is extracted with chloroform
11. 11
    Trocknenthe pooled organics are dried (sodium sulfate)
12. 12
    Filtrationfiltered
13. 13
    Einengenconcentrated under reduced pressure

Vorschrift

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]+.

Quelle