반응 #83134

반응 방정식

triethylamine

histamine dihydrochloride

2-adamantyloxycarbonyl-α-methyl-DL-tryptophan

pentafluorophenol

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

→

product

수율 47.3%

Tricyclo[3.3.1.13,7 ]dec-2-yl (±)-[2-[[2-(1H-imidazol-4-yl)ethyl]amino]-1-(1H -indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate

수율 47.3%

용매

ethyl acetate

ethyl acetate

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring an additional 40 hours
2. 2
   세척washed with water
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, 10% methanol/dichloromethane eluant)
6. 6
   기타dried for 48 hours under vacuum at 70° 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 pentafluorophenol (0.189 g, 1.03 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.200 g, 1.04 mmol). This mixture was stirred 2 hours, then triethylamine (0.36 mL, 2.6 mmol) and histamine dihydrochloride (0.240 g, 1.30 mmol) were added. After stirring an additional 40 hours, the resulting mixture was diluted with ethyl acetate (20 mL), and washed with water. The organic phase was dried over MgSO4, concentrated, purified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 10% methanol/dichloromethane eluant), and dried for 48 hours under vacuum at 70° C. to provide 0.234 g (47%) of product; 1H NMR (CDCl3) δ1.40-1.60 (2H, m), 1.57 (3H, s), 1.65-2.00 (13H, m), 2.65-2.75 (2H, m), 3.25-3.45 (4H, m), 4.82 (1H, br s), 5.42 ([H, br s), 6.67 (1H, s), 6.81 (1H, br s), 6.91 (1H, br s),7.00-7.20 (2H, m), 7.34 (1H, d, J 7 Hz), 7.46 (1H, s), 7.55 (1H, d, J 7 Hz), 8.67 (1H, br s).

출처