Potassium Carbonate → Methyl 4-[({2-[2-(4-bromobenzyloxy)phenyl]ethyl}-tert-butoxycarbonylamino)methyl]benzoate

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Reaction Steps

A solution of 5 g (12.87 mmol) of methyl 4-({tert-butoxycarbonyl-[2-(2-hydroxyphenyl)ethyl]amino}methyl)benzoate from Example 3A in 100 ml of dry acetonitrile is mixed with 3.89 g (15.57 mmol) of 4-bromobenzyl bromide and 2.69 g (19.46 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The resulting organic phase is concentrated. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1→10:1). 6.88 g (12.4 mmol, 89% yield) of a solid are obtained.

Provenance & Evidence