반응 #1751991

반응 방정식

sodium bicarbonate

ammonia

4-{[(benzyloxy)carbonyl]amino}-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

1-hydroxybenzotriazole hydrate

triethylamine

→

title compound

수율 20.6%

tert-Butyl 4-(aminocarbonyl)-4-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

수율 20.6%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   추출the mixture was extracted with ethyl acetate
2. 2
   건조The combined organic extracts were dried over magnesium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타Purification by silica gel chromatography (100% dichloromethane→94% dichloromethane/methanol)

실험 절차

To a solution of 4-{[(benzyloxy)carbonyl]amino}-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (2.09 g, 5.52 mmol) in N,N-dimethylformamide (10 mL) were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.27 g, 6.63 mmol), 1-hydroxybenzotriazole hydrate (0.37 g, 2.76 mmol) and triethylamine (0.92 mL, 6.63 mmol), followed by ammonia (0.5 M in dioxane; 13.3 mL, 6.63 mmol). After 18 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→94% dichloromethane/methanol) to give the title compound (0.43 g). MS 378.2 (M+1).

출처