Hydrochloric Acid → 2-[(4-{2-[Benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoic acid

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Reaction Steps

Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-methoxyphenoxy)methyl]benzoate (98 mg, 0.195 mmol) was dissolved in THF (2 ml). Lithium hydroxide (9.3 mg, 0.389 mmol) solved in water (1 ml) was added. The mixture was put in a microwave oven (Smith Synthesizer) at 150° C. for 7 minutes. It was then acidified with 1% hydrochloric acid, pH˜3, and extracted with ethyl acetate. The organic extract was washed with brine and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE®) SI, 2 g/6 ml) using DCM and then MeOH/DCM (0.5:99.5, then 1:99) as eluant gave 43 mg the desired product, yield 45%.

Provenance & Evidence