Aniline → 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)-N-phenylbenzamide

Participants

Reaction Steps

2-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid (35 mg, 0.0096 mmol) obtained in Step 6 of Example 22 was dissolved in tetrahydrofuran (4 mL) and dichloromethane (1 mL), and aniline (0.030 mL, 0.33 mmol), 1-hydroxybenzotriazole monohydrate (56 mg, 0.37 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.13 g, 0.68 mmol) were added to the obtained solution followed by stirring at a room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by preparative thin-layer chromatography (chloroform/methanol=100/1) to obtain 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)-N-phenylbenzamide (20 mg, 49%).

Provenance & Evidence