Reacción #42346

Ecuación de reacción

Boc-L-alanine

isobutylamine

diisopropylethylamine

HOBt

→

title compound

N1-Isobutyl-L-alaninamide

Disolventes

ethyl acetate

EDC

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
2. 2
   Secadodried (magnesium sulfate)
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated 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
   ConcentraciónThe solution is concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONdissolved in chloroform
9. 9
   Lavadowashed with 1 N NaOH (aq)
10. 10
    ExtracciónThe aqueous layer is extracted with chloroform
11. 11
    Secadothe pooled organics are dried (sodium sulfate)
12. 12
    Filtraciónfiltered
13. 13
    Concentraciónconcentrated under reduced pressure

Procedimiento

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]+.

Fuente