반응 #362325

반응 방정식

hydrochloric acid

methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate

cyclopentylacetic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

title compound

수율 73.0%

Methyl 4-[5-(2-cyclopentylacetamido)-1-methylindol-3-ylmethyl]-3-methoxybenzoate

수율 73.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   추출the separated aqueous layer extracted with dichloromethane (3×25 ml.)
2. 2
   세척the combined organic extracts washed with water, brine
3. 3
   건조dried (MgSO4)
4. 4
   기타evaporated
5. 5
   기타The residual oil was crystallized from ethyl acetate

실험 절차

A mixture of methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate (D) (0.57 g.), cyclopentylacetic acid (0.23 g.), 4-(dimethylamino)pyridine (0.22 g.), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.343 g.), was dissolved in dichloromethane (25 ml.), under an atmosphere of nitrogen, and stirred at room temperature for 18 hours. The mixture was poured into 1M hydrochloric acid (25 ml.), the separated aqueous layer extracted with dichloromethane (3×25 ml.), the combined organic extracts washed with water, brine, dried (MgSO4) and evaporated. The residual oil was crystallized from ethyl acetate to give the title compound (0.555 g. 73%) as a white powder; m.p. 180°-181° C.; partial NMR (250 MHz, DMSO-d6 ): 1.17(m,2H); 1.4-1.8 (m,6H); 2.25(m,3H); 3.70(s,3H, NMe); 3.82(s,3H, OMe); 3.92(s,3H, OMe); 3.97(s,2H, ArCH2); 9.62(br s, 1H, NH).

출처