반응 #83136

반응 방정식

triethylamine

2-furanethaneamine hydrochloride

2-adamantyloxycarbonyl-α-methyl-DL-tryptophan

1-hydroxybenzotriazole hydrate

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

→

desired product

수율 70.0%

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

수율 70.0%

용매

diethyl ether

water

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred for 21 hours at room temperature
2. 2
   기타partitioned between saturated aqueous NaHCO3 (50 mL) and ethyl acetate (50 mL)
3. 3
   추출The aqueous layer was extracted with ethyl acetate (20 mL)
4. 4
   세척The combined organic extracts were washed with aqueous 1M citric acid (3×15 mL), water (2×15 mL), saturated aqueous NaHCO3 (15 mL), water (15 mL), and saturated aqueous NaCl (15 mL)
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated in vacuo
7. 7
   기타to give a clear glass
8. 8
   농축methanol (5 mL), and water (2 mL), and concentrated in vacuo until a solid
9. 9
   기타formed
10. 10
    여과filtered
11. 11
    기타dried

실험 절차

A room temperature solution of 0.30 g (0.76 mmol) of 2-adamantyloxycarbonyl-α-methyl-DL-tryptophan and 0.11 g (0.81 mmol) of 1-hydroxybenzotriazole hydrate in 10 mL of anhydrous N,N-dimethylformamide under N2 atmosphere was treated with 0.16 g (0.83 mmol 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in one portion. The reaction was stirred for 1.75 hours at room temperature and treated with 0.09 g (0.93 mmol) of triethylamine and 0.13 g (0.88 mmol) of 2-furanethaneamine hydrochloride. The reaction was stirred for 21 hours at room temperature, then partitioned between saturated aqueous NaHCO3 (50 mL) and ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (20 mL). The combined organic extracts were washed with aqueous 1M citric acid (3×15 mL), water (2×15 mL), saturated aqueous NaHCO3 (15 mL), water (15 mL), and saturated aqueous NaCl (15 mL), dried over Na2SO4, and concentrated in vacuo. The residue was passed through a plug of SiO2 (70×230 mesh, 50% ethyl acetate-hexane eluant, 15 mL medium sintered glass funnel) to give a clear glass. The residue was dissolved in diethyl ether (3 mL), methanol (5 mL), and water (2 mL), and concentrated in vacuo until a solid formed. The mixture was treated with water, filtered, and dried to give 0.26 g (70%) of the desired product as a white solid, mp 87°-97° C.; 1H NMR (CDCl3) δ1.5-2.0 (17H, m), 2.67-2.74 (2H, m), 3.29 (1H, d, J 15 Hz), 3.46-3.49 (3H, m), 4.82 (1H, br s), 5.16 (1H, br s), 5.95 (1H, d, J 3 Hz), 6.25 (1H, dd, J 3 Hz and J 2 Hz), 6.37 (1H, br s), 6.97 (1H, d, J 2 Hz), 7.1-7.3 (3H, m), 7.36 (1H, d, J 8 Hz), 7.59 (1H, d, J 8 Hz), 8.18 (1H, br s).

출처