Benzenesulfonic Acid → Benzamide

Participants

Reaction Steps

First, 4-benzyloxy-3,5-dimethoxybenzoic acid chloride represented by Formula 85 (61.30 mg, 0.200 mmol) prepared in Preparative Example 1 and 4-(2-aminoethyl)morpholine represented by Formula 99 (31.22 mg, 0.240 mmol) were prepared in 0.2 M solution, respectively, using a toluene solvent. After adding 1M sodium carbonate solution and 0.2 M acyl chloride solution to the above solutions, the mixture was vigorously shaken and agitated at room temperature overnight. After terminating the reaction, an aqueous layer was discarded using a tip while an organic layer was moved to a cartridge tube (6 mL, benzenesulfonic acid, 904030-WJ, UCT) using ethyl acetate. Impurities were removed using methanol (15 mL), while separation and purification using an elute solution (ethyl acetate/methanol/triethylamine, 20:2:1, v/v/v) was conducted to produce a benzamide compound represented by Formula 7 as a desired product (VVZ-006; 79.10 mg, 98.8% yield).

Provenance & Evidence