Реакция #42346

Уравнение реакции

Boc-L-alanine

isobutylamine

diisopropylethylamine

HOBt

→

title compound

N1-Isobutyl-L-alaninamide

Растворители

ethyl acetate

EDC

DMF

Условия реакции

Обработка

1. 1
   Промывкаwashed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
2. 2
   Сушкаdried (magnesium sulfate)
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated 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
   КонцентрированиеThe solution is concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONdissolved in chloroform
9. 9
   Промывкаwashed with 1 N NaOH (aq)
10. 10
    ЭкстракцияThe aqueous layer is extracted with chloroform
11. 11
    Сушкаthe pooled organics are dried (sodium sulfate)
12. 12
    Фильтрацияfiltered
13. 13
    Концентрированиеconcentrated under reduced pressure

Методика

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]+.

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