반응 #83131

반응 방정식

triethylamine

2-thiopheneethaneamine hydrochloride

2-adamantyloxycarbonyl-α-methyl-DL-tryptophan

1-hydroxybenzotriazole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

→

product

수율 61.0%

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

수율 61.0%

용매

ethyl acetate

ethyl acetate

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring the resulting mixture 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
   농축concentrated
5. 5
   기타purified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 67% ethyl acetate/hexane eluant)
6. 6
   기타dried for 48 hours under vacuum at 60° C.

실험 절차

To a solution of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan (0.401 g, 1.01 mmol) in dry 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 (0.199 g, 1.04 mmol). this mixture was stirred 2 hours, then triethylamine (0.18 mL, 1.3 mmol) and 2-thiopheneethaneamine hydrochloride (0.214 g, 1.30 mmol) were added. After stirring the resulting mixture an additional 18 hours, the 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, concentrated, purified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 67% ethyl acetate/hexane eluant), and dried for 48 hours under vacuum at 60° C. to provide 0.310 g (61%) of product; 1H NMR (CDCl3) δ1.49-1.60 (2H, m), 1.55 (3H, s), 1.65-2.00 (12H, m), 2.88 (2H, t, J 6 Hz), 3.26 (1H, d, J 14 Hz), 3.40-3.60 (3H, m), 4.82 (1H, br s), 5.17 (1H, br s), 6.36 (1H, br s), 6.69 (1H, d, J 2 Hz), 6.85-6.90 (1H, m), 6.95 (1H, d, J 2 Hz), 7.00-7.22 (3H, m), 7.36 (1H, d, J 8 Hz), 7.58 (1H, d, J 8 Hz), 8.29 (1H, br s).

출처