反応 #50147

反応方程式

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

収率 67.5%

溶媒

dichloromethane

反応条件

後処理

1. 1
   洗浄The reaction mixture is washed with water
2. 2
   乾燥dried over sodium sulfate
3. 3
   その他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
   その他The solvent is evaporated
8. 8
   workup.ADDITIONthe residue is treated with a saturated sodium hydrogen carbonate solution
9. 9
   抽出extracted with chloroform
10. 10
    その他The organic layer is dried
11. 11
    その他evaporated
12. 12
    その他Purification by silica gel column chromatography (solvent; chloroform/methanol)

実験手順

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.

出典