반응 #11579

반응 방정식

sodium hydrogencarbonate

2-(1-adamantyl)-N-pentylethylamine hydrochloride

3-(t-Butoxycarbonylamino)propionic acid

N-methylmorpholine

isobutyl chlorocarbonate

→

3-(t-butoxycarbonylamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

수율 85.2%

용매

ethyl acetate

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타at −18° C
2. 2
   workup.STIRRINGThe whole was stirred at 0° C. for 1.5 hours
3. 3
   세척The organic layer was washed with a 10% aqueous citric acid solution (100 ml), water (100 ml)
4. 4
   건조a saturated aqueous sodium chloride solution (100 ml) successively and dried over anhydrous magnesium sulfate
5. 5
   농축The organic layer was concentrated under reduced pressure
6. 6
   기타the concentrate was purified by silica gel column chromatography

실험 절차

3-(t-Butoxycarbonylamino)propionic acid (1.0 g, 5.3 mmol) was dissolved in anhydrous tetrahydrofuran (15 ml), and N-methylmorpholine (0.6 ml, 5.5 mmol) was added to the solution. The mixture was stirred at −15° C., and isobutyl chlorocarbonate (0.7 ml, 5.4 mmol) was added thereto. Then, a solution of a free base of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1) (1.5 g, 5.3 mmol) in anhydrous tetrahydrofuran (15 ml) was added thereto at −18° C. The whole was stirred at 0° C. for 1.5 hours, ethyl acetate (100 ml) and a saturated aqueous sodium hydrogencarbonate solution (100 ml) were added to the reaction mixture, and the reaction mixture was distributed. The organic layer was washed with a 10% aqueous citric acid solution (100 ml), water (100 ml) and a saturated aqueous sodium chloride solution (100 ml) successively and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 1.9 g (85%) of 3-(t-butoxycarbonylamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide as an oily matter.

출처