반응 #3020

반응 방정식

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

수율 91.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   추출the aqueous phase is extracted with ethyl acetate
2. 2
   세척The organic extracts are washed with water
3. 3
   건조dried over anhydrous sodium sulphate
4. 4
   기타Evaporation of the solvent
5. 5
   기타leaves a yellow oil which
6. 6
   기타is purified by flash chromatography on a column of silica gel, eluent

실험 절차

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%.

출처