Reacción #1868388

Ecuación de reacción

2(2-aminoethyl)pyridine

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

2-adamantyloxycarbonyl-α-methyl-DL-tryptophan

1-hydroxybenzotriazole

→

product

Rendimiento 72.2%

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

Rendimiento 72.2%

Disolventes

ethyl acetate

ethyl acetate

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring an additional 18 hours
2. 2
   Lavadowashed with aqueous 1N citric acid, aqueous saturated sodium bicarbonate, and brine solutions
3. 3
   SecadoThe organic phase was dried over MgSO4
4. 4
   Concentraciónconcentrated
5. 5
   Otropurified by flash chromatography (SiO2, 230-400 mesh, ethyl acetate eluant)
6. 6
   ConcentraciónAfter concentration
7. 7
   Otrothe residue was dried under vacuum at 60° C. for 48 hours

Procedimiento

To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0.400 g, 1.01 mmol) in ethyl acetate (6 mL) and N,N-dimethylformamide (4 mL) under nitrogen atmosphere was added 1-hydroxybenzotriazole (0.138 g, 1.02 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.198 g, 1.03 mmol). This mixture was stirred 2 hours and 2(2-aminoethyl)pyridine (0.16 mL, 1.3 mmol) 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, aqueous saturated sodium bicarbonate, and brine solutions. The organic phase was dried over MgSO4, concentrated, and purified by flash chromatography (SiO2, 230-400 mesh, ethyl acetate eluant). After concentration, the residue was dried under vacuum at 60° C. for 48 hours to provide 0.365 g (72%) of product; 1H NMR (CDCl3) δ1.40-1.60 (2H, m), 1.56 (3H, s), 1.65-1.95 (12H, m), 2.88 (2H, t, J 6 Hz), 3.39 (2H, d, J 5 Hz), 3.50-3.70 (2H, m), 4.75 (1H, br s), 5.35 (1H, br s), 6.40 (1H, d, J 2 Hz), 7.00-7.20 (4H, m), 7.22-7.35 (2H, m), 7.52-7.60 (2H, m), 8.20 (1H, br s), 8.40-8.45 (1H, m).

Fuente