methyl (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoate hydrochloride → HCID 66696501, compound

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Reaction Steps

3-(3-Methoxy-4-hydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)-1-methoxycarbonylethyl]-2-propenamide synthesized from 5-hydroxy-L-tryptophan methyl ester hydrochloride (704 mg, 2.6 mmol) in the same manner as in Example 18 was dissolved in a mixed solvent of water (11.8 ml), 2.5N NaOH aqueous solution (11.8 ml), and N,N-dimethylformamide (23.6 ml) without purification, and the mixture was stirred at room temperature overnight. The reaction solvent was concentrated under reduced pressure, cooled to 0° C., and adjusted with 6N aqueous HCl solution to pH 1 to 2. The solution was extracted three times with ethyl acetate (30 ml), and the organic layer was washed with 3N HCl (20 ml) and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure, and purified by preparative thin-layer chromatography (PTLC, eluent: chloroform:methanol=3:1) to give 3-(3-methoxy-4-hydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)-1-hydroxycarbonylethyl]-2-propenamide (147 mg, yield 15.4%) as a powder.

Provenance & Evidence