2-Methyl-5-phenylfuran-3-carbonyl chloride → Methyl 2-[(4-{2-[(2-methyl-5-phenyl-3-furoyl)amino]ethyl)phenoxy)methyl]benzoate

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Reaction Steps

2-Methyl-5-phenylfuran-3-carbonyl chloride (36.4 mg, 0.165 mmol) and methyl 2-{[4-(2-aminoethyl)phenoxy]methyl}benzoate hydrochloride (53 mg, 0.165 mmol) were mixed in DCM (4 ml). PS-DIBA (3.66 mmol/g, 135 mg, 0.494 mmol) was added. The mixture was shaken at room temperature overnight. LC-MS showed there was only a trace amount of desired product and a big peak of 2-methyl-5-phenyl-3-furoic acid. TBTU (55 mg, 0.17 mmol) was added. The mixture was shaken for 2 hours and filtered. The filtrate was evaporated to dryness. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM and then MeOH/DCM (0.5:99.5) as eluant gave 34 mg the desired product, yield 44%.

Provenance & Evidence