Lithium Hydroxide → 2-[(4-{2-[Benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acid

Participants

Reaction Steps

Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate (70 mg, 0.148 mmol) in THF (2 ml) was cooled in an ice-bath. Lithium hydroxide (7.08 mg, 0.296 mmol) in water (1 ml) was dropped in. The cooling-bath was then removed and the mixture was stirred overnight. HPLC showed that the reaction was not complete. More lithium hydroxide (0.2M, 0.5 ml) was added. The reaction mixture was stirred for 4 days more. It was then evaporated in vacuum to remove THF. The residue was acidified with 1% hydrochloric acid, pH=3-4, and extracted with ethyl acetate. The organic phase was dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM, MeOH/DCM (1:99, and then 2:98) as eluant gave 24 mg the desired product, yield 35%.

Provenance & Evidence