Lithium hydroxide, monohydrate → 3-(1-{[3-Methoxy-4-(3-[2-methylphenyl]-ureido)-phenyl]-acetyl}-1,2,3,4-tetrahydro-quinolin-6-yl)-propionic Acid

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Reaction Conditions

Reaction Steps

A solution of ethyl 3-(1-{[3-methoxy-4-[(2-toluidinocarbonyl)amino]phenyl}acetyl)-1,2,3,4-tetrahydroquinolin-6-yl)-propanoate (0.24 g, Reference Example 1) in anhydrous ethanol (4 ml), at 20° C., was treated dropwise with a solution of lithium hydroxide monohydrate (33 mg) in distilled water (1 ml). After stirring for 3 hours at 20° C. the reaction mixture was evaporated under reduced pressure (2.7 kPa) at 40° C. The residue was treated with distilled water (35 ml) and the resulting solution was washed twice with diethyl ether (20 ml), then acidified to pH 3 by addition of hydrochloric acid (0.8 ml, 1N) and then extracted twice with ethyl acetate (25 ml). The combined organic extracts were washed twice with water (5 ml), then dried over magnesium sulfate and then evaporated under reduced pressure (2.7 kPa) at 40° C. The resulting white foamy solid (191 mg) was subjected to chromatography on silica gel plates (4 plates, 20×20 cm, thickness=0.5 mm), eluting with a mixture of dichloromethane and methanol (9:1, v/v) to give the title compound (148 mg) as a white foamy solid. 1H NMR (300 MHz, (CD3)2SO): δ 1.81 (m, 2H); 2.27 (s, 3H); from 2.45-2.70 (m, 4H), 2.82 (t, J=7.5 Hz, 2H); 3.72 (t, J=6.5 Hz, 2H); 3.82 (s, 2H); 3.87 (s, 3H); 6.60-7.50 (m, 8H); 7.82 (d, J=8 Hz, 1H); 8.05 (d, J=8 Hz, 1H); 8.50 (s, 1H); 8.60 (s, 1H). MS (Electron Impact recorded on a Finnigan SSQ 7000 spectrometer at 70 eV) 501 (M+).

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