반응 #83132

반응 방정식

2-(2-aminoethyl)-1-methylpyrrole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

2-adamantyloxycarbonyl-α-methyl-DL-tryptophan

1-hydroxybenzotriazole

→

Tricyclo[3.3.1.13,7 ]dec-2-yl (±)-[1-(1H-indol-3-ylmethyl)-1-methyl-2-[[2-(1-methyl-1H-pyrrol-2-yl) ethyl]amino]-2-oxoethyl]carbamate

용매

ethyl acetate

ethyl acetate

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring an additional 18 hours
2. 2
   세척washed with aqueous 1N citric acid, saturated aqueous sodium bicarbonate, and brine solutions
3. 3
   건조The organic phase was dried over MgSO4
4. 4
   기타purified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 67% ethyl acetate/hexane eluant)
5. 5
   농축Concentration
6. 6
   기타by drying under vacuum for 48 hours at 60° C.
7. 7
   기타provided 0.301 g (59%) at product

실험 절차

To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0.401 g, 1.01 mmol) in dry ethyl acetate (4 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added 1-hydroxybenzotriazole (0.139 g, 1.03 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.199 g, 1.04 mmol). This mixture was stirred 2 hours and 0.16 g (1.3 mmole) of 2-(2-aminoethyl)-1-methylpyrrole was added. After stirring an additional 18 hours, the resulting mixture was diluted with ethyl acetate (20 mL), and washed with aqueous 1N citric acid, saturated aqueous sodium bicarbonate, and brine solutions. The organic phase was dried over MgSO4 and purified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 67% ethyl acetate/hexane eluant). Concentration followed by drying under vacuum for 48 hours at 60° C. provided 0.301 g (59%) at product; 1H NMR (CDCl3) δ1.49-1.60 (2H, m), 1.56 (3H, s), 1.70-2.00 (12H, m), 2.61 (2H, t, J 7 Hz), 3.23-3.55 (4H, m), 3.50 (3H, s), 4.82 (1H, br s), 5.20 (1H, br s), 5.76 (1H, br s), 6.00 (1H, t, J 3 Hz), 6.34 (1H, br s), 6.53 (1H, br s), 6.97 (1H, br s), 7.09-7.19 (2H, m), 7.36 (1H, d, J 8 Hz), 7.59 (1H, d, J 8 Hz), 8.16 (1H, br s).

출처