反应 #42346

反应方程式

Boc-L-alanine

isobutylamine

diisopropylethylamine

HOBt

→

title compound

N1-Isobutyl-L-alaninamide

溶剂

ethyl acetate

EDC

DMF

反应条件

后处理

1. 1
   洗涤washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
2. 2
   干燥dried (magnesium sulfate)
3. 3
   过滤filtered
4. 4
   浓缩concentrated 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
   浓缩The solution is concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONdissolved in chloroform
9. 9
   洗涤washed with 1 N NaOH (aq)
10. 10
    萃取The aqueous layer is extracted with chloroform
11. 11
    干燥the pooled organics are dried (sodium sulfate)
12. 12
    过滤filtered
13. 13
    浓缩concentrated under reduced pressure

实验过程

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]+.

来源