Hydrochloric Acid → (+/-) 1-(3-Acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic Acid

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Reaction Steps

A solution of (±)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid hydrochloride (14.52 g) in pyridine (150 ml) was treated dropwise with 3-acetylthio-2-(acetylthiomethyl)propanoyl chloride with vigorous stirring. After stirring overnight at room temperature, the mixture was added to ice (300 g) and the pH was adjusted to 2.5 with concentrated hydrochloric acid. The mixture was extracted with ether and the ether extract dried over sodium sulfate and evaporated to a syrup. This (±) 1-(3-acetylthio-2-acetylthiomethyl-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid was further purified by column chromatography (silica gel, toluene:ethyl acetate:acetic acid, 6.5:3:0.5); yield 2.5 g, m.p. 149°-151°.

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