Hydrochloric Acid → Methyl 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

Participants

Reaction Steps

Cyclopentyl chloroformate (0.11 g) was added to a stirred solution of methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate (S) (0.25 g) and N-methylmorpholine (0.23 g) in dichloromethane (3 ml), under an atmosphere of nitrogen. The mixture was stirred for 2 hours and then poured into 1M hydrochloric acid (20 ml). This acid mixture was extracted with ethyl acetate (2×30 ml). The combined extracts were washed with saturated brine (20 ml), dried (MgSO4), and evaporated to give a viscous oil. This was purified by flash chromatography on silica gel (50 ml), eluting with 3:7 v/v ethyl acetate:hexane, to give methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methyl-indol-3-ylmethyl]-3-methoxybenzoate (T) as a foam (0.25 g, 74%); NMR: 1.62[m, 8H, (CH2)4 ], 3.68(s, 3H, NCH3), 3.83(s, 3H, COOCH3), 3.91(s, 3H, OCH3), 3.95(s, 2H, CH2Ar), 5.05(m, 1H, --CHO--), 7.11(m, 2H), 7.26(d, 1H), 7.43 (m, 2H), 7.59(br, 1H), 9.18 (br, 1H, NH).

Provenance & Evidence