تفاعل #3020

معادلة التفاعل

BOP

triethylamine

1-(methoxycarbonylmethyl)-2-indolecarboxylic acid

[(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylamine hydrochloride

compound 100

[(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylamine hydrochloride

water

→

methyl{2-[[(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylcarbamoyl]-1-indolyl}acetate

المردود 91.0%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe aqueous phase is extracted with ethyl acetate
2. 2
   غسيلThe organic extracts are washed with water
3. 3
   تجفيفdried over anhydrous sodium sulphate
4. 4
   أخرىEvaporation of the solvent
5. 5
   أخرىleaves a yellow oil which
6. 6
   أخرىis purified by flash chromatography on a column of silica gel, eluent

الإجراء التجريبي

0.8 9 of [(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylamine hydrochloride (compound 100) is dissolved in 10 ml of dimethylformamide and 0.58 g of 1-(methoxycarbonylmethyl)-2-indolecarboxylic acid, 1.12 g of BOP and then, dropwise, 0.75 g of triethylamine are successively added to the reaction mixture at room temperature. The reaction mixture is left at room temperature for 20 hours, is then poured into cold water and the aqueous phase is extracted with ethyl acetate. The organic extracts are washed with water and then dried over anhydrous sodium sulphate. Evaporation of the solvent leaves a yellow oil which is purified by flash chromatography on a column of silica gel, eluent: dichloromethane/methanol 98/2 (v/v) in order to obtain white crystals of methyl{2-[[(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylcarbamoyl]-1-indolyl}acetate; M.p.=141° C.; Yield: 91%.

المصدر