反应详情

To a solution of 4-(carboethoxymethyl)indole (830 mg, 4.12 mmol) and ethyl bromopyruvate 2-oxime (866 mg, 4.12 mmol) in methylene chloride (40 mL) was added anhydrous Na2CO3 (2.40 g, 22.66 mmol) at ambient temperature. After stirring at ambient temperature for 16 hours, the mixture was filtered and concentrated to dryness. The residue was chromatographed on silica gel eluted with 10% MeOH in CHCl3 /hexane (1:1→2:1) to give 0.98 g of the title compound. TLC Rf=0.61 (10%MeOH/CHCl3). MS(DCl) m/e 333 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.25(t, J=7.4 Hz, 3H), 1.30(t, J=7.4 Hz,3H), 4.13(s,2H), 4.18(q, J=7.4 Hz,2H), 4.28(q, J=7.4 Hz,2H), 4.28(q, J=7.4 Hz,2H), 4.30(s,2H), 6.92(br s, 1H), 6.98(d, J=7.4 Hz, 1H), 7.12(t, J=7.4 Hz, 1H), 7.26(d,J=7.4 Hz, 1H), 8.03(br s, --OH), 8.17 (br s, --NH).

1. filtrationthe mixture was filtered
2. concentrationconcentrated to dryness
3. customThe residue was chromatographed on silica gel
4. washeluted with 10% MeOH in CHCl3 /hexane (1:1→2:1)