Dichloromethane → HCID 19870586, compound

Participants

Reaction Steps

Methyl 4-[5-[1-hydroxy-2-(propylcarbamoyl)butyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.75 g, as a mixture of diastereomers) was combined with acetic anhydride (0.31 g), triethylamine (0.152 g), and methylene chloride (20 ml), under a nitrogen atmosphere, and the mixture heated under reflux for 20 hr. The cooled mixture was diluted with ethyl acetate, washed (1M hydrochloric acid (twice), water, brine), dried (MgSO4) and evaporated to give a dark oil. The product was purified by flash chromatography, eluting with 8:2 methylene chloride:ethyl acetate, to give methyl 4-[5-[1-acetoxy-2-(propylcarbamoyl)butyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.69 g, 85%, as a mixture of diastereomers) as an oil: partial NMR (300 MHz, DMSO-d6): 0.40(t, 3H, CH3, one isomer), 0.66(t, 3H, CH3, other isomer), 0.79(m, 12H, 2×CH3, one isomer, 2×CH3, other isomer), 1.84(s, 3H, OCOCH3, one isomer), 1.97(s, 3H, OCOCH3, other isomer), 5.66 (d, 1H, CHOCOCH3, one isomer), 5.79(d, 1H, CHOCOCH3, other isomer), 7.67(br t, 1H, NH, one isomer), 8.04(br t, 1H, NH, other isomer).

Provenance & Evidence