Dl-Tryptophan → HCID 67359615, compound

Participants

Reaction Steps

In close analogy to the procedure described in Example 32, 2,6-dichloro-8-methyl-quinoline-3-carboxylic acid ethyl ester is reacted with DL-tryptophan to provide 2-[1-carboxy-2-(1H-indol-3-yl)-ethylamino]-6-chloro-8-methyl-quinoline-3-carboxylic acid ethyl ester. The ester (107 mg, 0.24 mmol) is dissolved in THF (2 mL), then 0.7M aqueous NaOH (1 mL) is added and the mixture is stirred at rt for 23 h. The mixture is concentrated under reduced pressure treated with water and filtered. The filtrate is acidified by addition of 3N HCl till pH 2-3, and stirred for 40 min. Precipitate is filtered off and washed with cold water to provide after drying the title compound (55 mg, 61%) as pale green powder.

Provenance & Evidence