Potassium Hydroxide → JWH 250 N-pentanoic acid metabolite

Participants

Reaction Steps

Ethyl 5-(3-(2-(2-methoxyphenyl)acetyl)-1H-indol-1-yl)pentanoate [Ethyl N-(carboxybutyrate) JWH-250] 7 (856 mg, 2.18 mmol) was dissolved in tertahydrofuran (15 ml) and water (15 ml) was added followed by potassium hydroxide (287 mg, 4.36 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo, the residue was acidified to pH 3 and extracted three times with ethyl acetate (3×50 ml). The organic fractions were combined, dried over sodium sulphate and concentrated under vacuo. The residue was purified by column chromatography (silica gel, 50%-100% ethyl acetate in hexane) and then recrystalised from ethylacetate/hexane to give 565 mg (71%) 5-(3-(2-(2-methoxyphenyl)acetyl)-1H-indol-1-yl)pentanoic acid [N-(carboxybutyric acid) JWH-250] (Hapten 2) as a white solid.

Provenance & Evidence