Triethylamine → Methyl 6-(2-phenoxyacetylamino)hexanoate

Beteiligte Stoffe

Reaktionsschritte

To phenoxyacetic acid (50.0 g, 0.33 mol) dissolved in tetrahydrofuran (210 mL) was slowly added 1,1′-carbonyldiimidazole (56.0 g, 0.35 mol) with additional tetrahydrofuran (30 mL). After stirring for 1.5 hr at room temperature, triethylamine (92 mL, 0.66 mol) was added all at once and methyl 6-aminohexanoate hydrochloride (66.0 g, 0.36 mol) was added in portions over 20 min. The reaction mixture was stirred at room temperature overnight, heated at 50° C. for 20 min, and then stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, added to 1 N hydrochloric acid (750 mL) and extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with 1 N hydrochloric acid (1×100 mL), water (1×100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a yellow oil. NMR analysis indicated presence of phenoxyacetic acid. The concentrate was dissolved in toluene (450 mL) and stirred 15 min with 25% sodium bicarbonate (200 mL). The organic layer was filtered through 1 PS paper, concentrated under reduced pressure, diluted with hexanes, and concentrated again, to give 76.89 g (84%) of the title compound, amide, as a yellow oil.

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