تفاعل #614926

معادلة التفاعل

(2S,4S)-1-(tert-butoxycarbonyl)-4-((4-(methoxycarbonyl)benzyl)oxy)pyrrolidine-2-carboxylic acid

EDC

3H-[1,2,3]-triazolo[4,5-b]pyridin-3-ol

(R)-1,2,3,4-tetrahydronaphthalen-1-amine

4-methylmorpholine

→

title compound

المردود 81.0%

(2S,4S)-tert-Butyl 4-((4-(methoxycarbonyl)benzyl)oxy)-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidine-1-carboxylate

المردود 81.0%

المذيبات

DMF

ethyl acetate

brine

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 1 h
2. 2
   أخرىThe organic layer was separated
3. 3
   غسيلwashed successively with aq. NaHCO3 solution, brine, and 1N HCl solution
4. 4
   تجفيفThe organics were dried over MgSO4
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe resulting residue was purified by flash chromatography (eluting with 20% EtOAc/DCM)

الإجراء التجريبي

To a solution of (2S,4S)-1-(tert-butoxycarbonyl)-4-((4-(methoxycarbonyl)benzyl)oxy)pyrrolidine-2-carboxylic acid (1.2 g, 3.2 mmol) in DMF (10 mL) was added EDC (0.91 g, 4.7 mmol) and 3H-[1,2,3]-triazolo[4,5-b]pyridin-3-ol (0.43 g, 3.2 mmol). The reaction mixture was stirred at rt for 5 min and treated with a solution of (R)-1,2,3,4-tetrahydronaphthalen-1-amine (0.54 g, 3.6 mmol) in DMF (5 mL) and 4-methylmorpholine (0.70 mL, 6.3 mmol). The reaction mixture was stirred at rt for 1 h and diluted with ethyl acetate and brine. The organic layer was separated and washed successively with aq. NaHCO3 solution, brine, and 1N HCl solution. The organics were dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by flash chromatography (eluting with 20% EtOAc/DCM) to afford the title compound as a white solid (1.3 g, 81%). 1H NMR (CDCl3) δ 7.99 (d, J=8.4 Hz, 2H), 7.33 (d, J=6.8 Hz, 2H), 7.13-6.94 (m, 3H), 6.85-6.80 (m, 1H), 5.21-5.01 (m, 1H), 4.49-4.33 (m, 2H), 4.11 (d, J=3.1 Hz, 1H), 3.93 (s, 3H), 3.70-3.41 (m, 2H), 2.74 (d, J=3.3 Hz, 2H), 2.05 (s, 2H), 1.90-1.68 (m, 3H), 1.58 (s, 1H), 1.45 (s, 10H); MS(ESI+) m/z 509.5 (M+H)+.

المصدر