Hydrochloric Acid → N-(heptan-4-yl)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide

Participants

Reaction Steps

A solution of dicyclohexyl carbodiimide (DCC) (5.5 g, 26.7 mmol) in 1,4-dioxane (50 ml) was added to a stirred solution of 4-hydroxy-3-methoxymandelic acid (5 g, 25.3 mmol) and N-hydroxysuccinimide (3 g, 26.1 mmol) in 1,4-dioxane (100 ml) at room temperature. The resulting white suspension was stirred at room temperature for 16 hours. Then the reaction mixture was filtered. The filtrate was poured into a stirred solution of 4-heptylamine in water (20 ml) and sodium bicarbonate (2.5 g, 20 mmol) was added. The resulting solution was heated to 50° C. and stirred at this temperature for 1.5 hour. The cooled solution was acidified to pH<2 using aq. HCl 5% solution and extracted three times with ethyl acetate (100 ml). The combined organic layers were washed with brine, dried with sodium sulfate, filtered and the filtrate concentrated by evaporation under reduced pressure. The residue was purified by crystallization from ethyl acetate/heptane to yield the title product (5.5 g, 73.6%) as white crystals.

Provenance & Evidence