Methanol → t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-carboxypropyl)indol-1-ylmethyl]-3-methoxybenzoate

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Reaction Steps

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonylpropyl)indol-1-ylmethyl]-3-methoxybenzoate (0.75 g) in a mixture of tetrahydrofuran (3.5 ml), methanol (3.5 ml), and water (1.3 ml) was treated with lithium hydroxide monohydrate (0.33 g). The mixture was stirred at 30° for 6 hours and then concentrated to remove the organic solvents. The residue was dissolved in water, and the solution was acidified with 10% (v/v) hydrochloric acid. The precipitate which formed was collected by filtration and dried to give t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-carboxypropyl)indol-1-ylmethyl]-3-methoxybenzoate (0.68 g, 95%) as a white powder; mp 195°-197°; partial NMR (80 MHz, CDCl3): 2.55-3.24(m, 3H, CH2CHCH3), 3.38(t, 2H, NHCH2), 3.91(s, 3H, OCH3), 5.24(s, 2H, NCH2), 6.17(br t, 1H, NH), 6.61(d, 1H, Ar), 7.04(s, 1H, H2 -indole), 7.85(br s, 1H, H7 -indole).

Provenance & Evidence