반응 #320816

반응 방정식

2-adamantyl oxycarbonyl-α-methyl DL tryptophane

hydroxybenzothiazole hydrate

triethyl amine

→

title compound

Tricyclo[3.3.1.13,7 ]dec-2-yl (±)-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(9H-xanthen-9-ylmethyl)amino]ethyl]carbamate

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   농축The clear solution was concentrated in vacuo
3. 3
   세척The ethyl acetate solution was washed with 1 NHCl, saturated NdHCO3 and brine
4. 4
   건조The organic phase was dried over MgSO4
5. 5
   농축concentrate in vacuo
6. 6
   기타to give a white foam
7. 7
   기타The product was chromatographed over silica using 50% ethyl acetate

실험 절차

A solution of 2-adamantyl oxycarbonyl-α-methyl DL tryptophane (0.79 g, 0.002 mmol) in methylene chloride (60 mL) was treated with hydroxybenzothiazole hydrate (0.3 g, 0. 0022 mmol), 1-(2-dimethylamino propyl)-3-ethylcarbodiimide. HCl (0.38 g, 0.002 mmol) and triethyl amine (0.202 g, 0.002 mmol). After stirring at room temperature for 2 hours a solution of 3H-xanthane-9-methenamine (0.495 g, 0.002 mmol) in methylene chloride (10 mL) was added. The reaction mixture was stirred at room temperature overnight. The clear solution was concentrated in vacuo. The resulting oil was taken up in ethyl acetate. The ethyl acetate solution was washed with 1 NHCl, saturated NdHCO3 and brine. The organic phase was dried over MgSO4 and concentrate in vacuo to give a white foam. The product was chromatographed over silica using 50% ethyl acetate; 50% hexane as eluant to give the title compound (0.72 g, 59%).

출처