反応 #3020

反応方程式

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

収率 91.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   抽出the aqueous phase is extracted with ethyl acetate
2. 2
   洗浄The organic extracts are washed with water
3. 3
   乾燥dried over anhydrous sodium sulphate
4. 4
   その他Evaporation of the solvent
5. 5
   その他leaves a yellow oil which
6. 6
   その他is purified by flash chromatography on a column of silica gel, eluent

実験手順

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%.

出典