Propanal → HCID 66941722, compound

Participants

Reaction Conditions

Reaction Steps

In methanol (4.5 ml), 4-aminomethylbenzoic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (300 mg) was dissolved. Then, trimethyl orthoformate (300 μl) and sodium cyanoborohydride (501 mg) were added to the solution, and then the whole was cooled to 0° C. Subsequently, the solution was added with propionaldehyde (357 ml) and then stirred at room temperature for 6 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and then washed with a 1 mol/l sodium hydroxide aqueous solution. After that, chloroform was added. The aqueous layer was neutralized with 1 mol/l hydrochloric acid and extraction with chloroform was then carried out. The solvent was distilled off under reduced pressure and the residue was then dried under vacuum, thereby obtaining a crude product (193.3 mg) as a white viscous solid. Subsequently, the crude product was dissolved in DMF (3.0 ml) and then added with WSCI hydrochloride (236 mg) and HOBt (167 mg), followed by stirring at room temperature for 30 minutes. After that, the solution was added with the compound (183 mg) obtained in Example 71-1 and then stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and then washed with water, a 1 mol/l sodium hydroxide aqueous solution, and saturated saline solution, followed by drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (213 mg) as a pale-yellow viscous liquid.

Provenance & Evidence