Sodium Hydroxide → [4-(4-dipropylaminomethylphenylcarbamoyl)benzyl]carbamic Acid t-butyl Ester

Participants

Reaction Steps

Commercially available 4-(t-butoxycarbonylamino-methyl)-benzoic acid (manufactured by Watanabe Chemical Industries, Ltd.) (1.16 g) was dissolved in chloroform (20 ml) and then added with WSCI hydrochloride (1.21 g), HOBt (963 mg), and the compound (865 mg) obtained in Example 15-2, and the whole was stirred overnight at room temperature. After completion of the reaction, a 1 mol/l sodium hydroxide aqueous solution was added thereto and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated aqueous ammonium chloride solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off. The residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (545 mg) as a yellow solid.

Provenance & Evidence