Hydrochloric Acid → {2-[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]ethylamino}acetic acid

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Reaction Steps

Compound 2 (0.28 g, 0.71 mmol) dissolved in THF (5 mL) was treated with LiOH (89 mg, 2.13 mmol, dissolved in 2 mL water) at room temperature overnight. The reaction mixture was neutralized with 2 N HCl aqueous solution to pH 5, and concentrated under vacuum. The resulting residue was co-evaporated with ethanol twice, and then loaded onto silica gel in a column. The product was eluted with a mixture of methanol (0-22%), ammonium hydroxide (0-2.2%) and dichloromethane (100-75.8%) to afford the desired product 11 (0.25 g, 96% yield) as a white solid. 1H NMR (500 MHz, CD3OD) δ 1.42 (s, 9H), 1.48 (m, 2H), 1.62 (m, 2H), 2.58 (t, 2H), 3.06 (m, 2H), 3.45 (m, 2H), 3.70 (s, 2H), 4.26 (m, 2H), 6.90 (d, 2H), 7.16 (d, 2H). m/z (ESI) 367.

Provenance & Evidence