تفاعل #50147

معادلة التفاعل

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

المردود 67.5%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   غسيلThe reaction mixture is washed with water
2. 2
   تجفيفdried over sodium sulfate
3. 3
   أخرىevaporated
4. 4
   workup.DISSOLUTIONThe residue is dissolved in ethanol (30 ml)
5. 5
   workup.ADDITIONfumaric acid (2.00 g) is added
6. 6
   درجة الحرارةthe solution is refluxed for three hours
7. 7
   أخرىThe solvent is evaporated
8. 8
   workup.ADDITIONthe residue is treated with a saturated sodium hydrogen carbonate solution
9. 9
   استخلاصextracted with chloroform
10. 10
    أخرىThe organic layer is dried
11. 11
    أخرىevaporated
12. 12
    أخرىPurification by silica gel column chromatography (solvent; chloroform/methanol)

الإجراء التجريبي

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.

المصدر