Methyl Acrylate → 3-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]amino]propanoic acid methyl ester

Participants

Reaction Steps

A solution of 147 mg (0.5 mmol) of 5-amino-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide (Example 18) and 2 mL of methyl acrylate in 5 mL of MeOH was stirred for 65 hours, then concentrated at reduced pressure. The residue was chromatographed on silica and eluted with a gradient (EtOAc→45% MeOH/EtOAc) to give a major product and a minor product in the later fractions. The major product was 105 mg (55% yield) of 3-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]amino]propanoic acid methyl ester.

Provenance & Evidence