Dicyclohexylcarbodiimide → 6-[5-(1-Pyrenecarbonylamino)-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]-hexadeca-1(16),12,14-triene

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Reaction Steps

A solution of 1-pyrenecarboxylic acid (0.22 g, 0.89 mmol) and 4-methymoroholine (0.12 g, 1.14 mmol) in 5 mL of anhydrous THF was stirred for 30 min. After addition of DCC (0.16 g, 0.76 mmol) and HOBT (0.11 g, 0.76 mmol), the solution was stirred another 30 min. A solution of 6-(5-amino-1-pentanyl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (0.51 g, 0.76 mmol) was added into the above solution and stirred at rt overnight. The solvent was evaporated and the residue was dissolved in CH2Cl2. The resulting solution was washed with 5% NaHCO3 solution and brine, dried and concentrated. The residue was purified by flash chromatography on a silica gel column using 100:1 CH2Cl2—MeOH as an eluent to give 0.45 g (65%) of the title compound as a yellow foam.

Provenance & Evidence