Hydrochloric Acid → HCID 66812088, compound

Participants

Reaction Steps

N-Ethyl-N,N-diisopropylamine (388 μL, 2.23 mmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (615 mg, 2.22 mmol) were added to a solution of ethanol (10 mL) containing 4-{2-[4-(dimethylamino)phenyl]ethoxy}benzoic acid (567 mg, 1.99 mmol) prepared in Example 23 (23a) and glycine methyl ester hydrochloride (280 mg, 2.23 mmol). The mixture was stirred at room temperature for 18 hours, and a saturated sodium hydrogen carbonate aqueous solution was added thereto to terminate the reaction. The mixture was extracted with ethyl acetate twice, and the organic layers were dried over anhydrous magnesium sulfate. Then, the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1 to 2:5, v/v) to give an oily compound. To a solution of ethanol (6 mL) containing the resulting compound, a 2 M lithium hydroxide aqueous solution (1.60 mL, 3.20 mmol) was added. The mixture was stirred at 60° C. for 40 minutes, and then 10% hydrochloric acid (3.5 mL) was added thereto under ice-cooling. The mixture was extracted with ethyl acetate, and the organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 395 mg of the title compound (white powder, yield: 58%)

Provenance & Evidence