Hydrochloric Acid → N2-(3-chloro-2-methylphenyl)-N2-{[4-(hydroxymethyl)phenyl]sulfonyl}-N-(4-methoxybenzyl)glycinamide

Participants

Reaction Steps

300 mg of 4-[((3-chloro-2-methylphenyl){2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)sulfonyl]benzoic acid was dissolved in 5.00 mL of THF, and 340 mg of ethyl chloroformate and 326 mg of triethylamine were added thereto, followed by stirring at room temperature for 1 hour. To the reaction liquid was added dropwise an aqueous solution (0.80 mL) of 360 mg of sodium borohydride over 30 minutes, followed by stirring at room temperature for 2 hours. The reaction liquid was acidified with addition of 8.0 mL of 1 M hydrochloric acid, and then extracted with a mixed solvent of chloroform/methanol (5/1), and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10) to obtain a product, which was crystallized from diisopropyl ether to obtain 118 mg of N2-(3-chloro-2-methylphenyl)-N2-{[4-(hydroxymethyl)phenyl]sulfonyl}-N-(4-methoxybenzyl)glycinamide.

Provenance & Evidence