Water → HCID 57587039, compound

Participants

Reaction Steps

A solution containing 19.6 mg (0.04 mmol) of (S)-(+)-N-acetyl-2,4,6-tribromo-5-methoxytryptophan methyl ester (4) dissolved in 1.5 mL of N,N-dimethylformamide was charged with 18.0 mg (0.13 mmol) of potassium carbonate and subsequently with 0.09 mL (d =1.44,0.7 mmol) of benzyl bromide. The mixture was stirred at room temperature for 30 minutes. The reaction solution was charged with water and subjected to extraction with an ethyl acetate-methanol (95:5, v/v) mixed solvent. The organic phase was washed with a saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain yellow oil. Thin-layer chromatography using silica gel as a carrier and a chloroform-methanol (99:1, v/v) mixed solvent as a developing solvent was performed. A band having an Rf value of 0.18 to 0.29 was extracted with a chloroform-methanol (95:5, v/v) mixed solvent to obtain the substance of interest (8) at a yield of 22.0 mg (96%).

Provenance & Evidence