反应 #50147

反应方程式

ethyl 2-ethyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate

monoethyl malonate

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

triethylamine

→

ethyl 2-ethyl-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl-5-ethoxycarbonylacetyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate

收率 67.5%

溶剂

dichloromethane

反应条件

后处理

1. 1
   洗涤The reaction mixture is washed with water
2. 2
   干燥dried over sodium sulfate
3. 3
   其他evaporated
4. 4
   workup.DISSOLUTIONThe residue is dissolved in ethanol (30 ml)
5. 5
   workup.ADDITIONfumaric acid (2.00 g) is added
6. 6
   温度the solution is refluxed for three hours
7. 7
   其他The solvent is evaporated
8. 8
   workup.ADDITIONthe residue is treated with a saturated sodium hydrogen carbonate solution
9. 9
   萃取extracted with chloroform
10. 10
    其他The organic layer is dried
11. 11
    其他evaporated
12. 12
    其他Purification by silica gel column chromatography (solvent; chloroform/methanol)

实验过程

A solution of ethyl 2-ethyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (1.94 g), monoethyl malonate (0.74 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.80 g), triethylamine (1.40 g) in dichloromethane (20 ml) is stirred overnight at room temperature. The reaction mixture is washed with water and dried over sodium sulfate, and then evaporated. The residue is dissolved in ethanol (30 ml), fumaric acid (2.00 g) is added, and the solution is refluxed for three hours. The solvent is evaporated and the residue is treated with a saturated sodium hydrogen carbonate solution and then extracted with chloroform. The organic layer is dried and evaporated. Purification by silica gel column chromatography (solvent; chloroform/methanol) gives ethyl 2-ethyl-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl-5-ethoxycarbonylacetyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (1.07 g) as a foam.

来源