Lithium hydroxide, monohydrate → 3-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoic acid

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Reaction Steps

Methyl 3-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)propanoate (2.00 g, 5.41 mmol) was dissolved in THF (5 mL), and a solution of lithium hydroxide monohydrate (469 mg, 11.18 mmol) in water (1 mL) was added at room temperature. The resulting mixture was stirred at room temperature for 18 hours. The mixture was concentrated in vacuo to remove most of the THF, and the resulting aqueous phase was acidified to pH 3 with 2 M aqueous HCl. The resulting cloudy mixture was extracted with CH2Cl2 (3×10 mL), and the combined organic phases were washed with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo to a white solid. The solid was further dried under high vacuum overnight to provide the title compound as an off-white powder (1.79 g, 5.04 mmol, 93% yield). 1H NMR (DMSO-d6) δ 2.60 (t, J=7.0 Hz, 2H), 2.82 (t, J=7.2 Hz, 2H), 5.26 (s, 2H), 6.62 (s, 1H), 6.89 (dd, J=7.8, 5.1 Hz, 1H), 7.35 (m, 4H), 7.57 (s, 1H), 7.58 (m, 1H), 7.86 (dd, J=1.5, 5 Hz, 1H), 9.96 (br s, 1H), 12.14 (br s, 1H); Mass spectrum (apci) m/z 354.0 (M−H).

Provenance & Evidence