Diisopropylethylamine → (3-{[(4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-tetrahydro-2H-pyran-4-yl)carbonyl]amino}propyl)(triphenyl)phosphonium bromide

Participants

Reaction Steps

4-{[(tert-Butoxycarbonyl)(methyl)amino]methyl}tetrahydro-2H-pyran-4-carboxylic acid (549 mg, 2.01 mmol) was dissolved in N,N-dimethylformamide (5.5 mL). To this solution were added N,N-diisopropylethylamine (385 μL, 2.21 mmol), 1-hydroxybenzotriazole hydrate (323 mg, 2.11 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (578 mg, 3.01 mmol), and (3-ammoniopropyl)(triphenyl)phosphonium dibromide (1.16 g, 2.41 mmol). The reaction mixture was stirred overnight at room temperature, then diluted with methylene chloride and washed with 5% aqueous lithium chloride (3 times), 1N aqueous hydrogen chloride, and saturated sodium bicarbonate. The organic solution was dried over anhydrous sodium sulfate, filtered, and concentrated to give crude the title compound. The crude product was purified on a silica gel column eluting with 10% methanol with methylene chloride to isolate the title compound (729 mg, 55.4% yield).

Provenance & Evidence