Reaktion #83134

Reaktionsgleichung

triethylamine

histamine dihydrochloride

2-adamantyloxycarbonyl-α-methyl-DL-tryptophan

pentafluorophenol

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

→

product

Ausbeute 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

Ausbeute 47.3%

Lösungsmittel

ethyl acetate

ethyl acetate

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring an additional 40 hours
2. 2
   Waschenwashed with water
3. 3
   TrocknenThe organic phase was dried over MgSO4
4. 4
   Einengenconcentrated
5. 5
   Sonstigepurified by flash chromatography (SiO2, 4×20 cm, 230-400 mesh, 10% methanol/dichloromethane eluant)
6. 6
   Sonstigedried for 48 hours under vacuum at 70° C.

Vorschrift

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).

Quelle