Diisopropylethylamine → 5-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ((S)-1-hydroxymethyl-propyl)-amide

Participants

Reaction Steps

To a solution of 5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid (75 mg, 0.22 mmol) in THF (2 mL) was added 1-hydroxy-benzotriazole hydrate (34.1 mg, 0.22 mmol), N-ethyldiisopropylamine (95.2 μL, 0.55 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (42.6 mg, 0.22 mmol) and S-(+)-1-amino-2-propanol (16.7 mg, 0.22 mmol). The reaction mixture was stirred overnight at room temperature. Evaporation of the mixture followed by chromatography (silica, dichloro-methane:methanol=1:0 to 9:1) afforded the title compound (50 mg, 55%) as a colourless gum. MS: m/e=416.2 [M+H]+.

Provenance & Evidence