تفاعل #42346

معادلة التفاعل

Boc-L-alanine

isobutylamine

diisopropylethylamine

HOBt

→

title compound

N1-Isobutyl-L-alaninamide

المذيبات

ethyl acetate

EDC

DMF

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
2. 2
   تجفيفdried (magnesium sulfate)
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated 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
   تركيزThe solution is concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONdissolved in chloroform
9. 9
   غسيلwashed with 1 N NaOH (aq)
10. 10
    استخلاصThe aqueous layer is extracted with chloroform
11. 11
    تجفيفthe pooled organics are dried (sodium sulfate)
12. 12
    ترشيحfiltered
13. 13
    تركيزconcentrated under reduced pressure

الإجراء التجريبي

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]+.

المصدر