Methanol → HCID 10800561, compound

Participants

Reaction Steps

Thionyl chloride (1.0 mL, 13.7 mmol) was added dropwise to a slurry of 5-methoxy-DL-tryptophan (2.0 g, 8.54 mmol) in anhydrous methanol (22 mL) at 0° C. under a nitrogen blanket. The resulting solution was warmed slowly to room temperature, stirred for 17 hours, then the solvent was removed under reduced pressure. The resulting residue was dissolved in water (20 mL), neutralized with saturated NaHCO3 (10 mL), and extracted twice with methylene chloride. The combined organic layers were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to provide 5-methoxy-DL-tryptophan methyl ester (Intermediate 4) as a light brown solid (1.55 g, 73%): 1H NMR (300 MHz, CDCl3): δ 7.93 (bs, 1H), 7.30-7.25 (m, 1H), 7.09-7.03 (m, 1H), 6.90-6.83 (m, 1H), 3.90-3.78 (m, 4H), 3.72 (s, 3H), 3.30-3.20 (m, 1H), 3.10-2.98 (m, 1H).

Provenance & Evidence