Hydrochloric Acid → 3-methoxy-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoic acid

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To a solution of ethyl 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate (550 mg, 0.98 mmol) in THF (15 mL) was added 0.25 N NaOH (15 mL). The resulting mixture was then heated under reflux for 2 days. The mixture was poured into 1 N HCl and the solid was collected. The crude solid was recrystallized from EtOH—CHCl3 to give 182 mg (35%) 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoic acid 256 as a white crystalline powder. mp 115–118° C.; IR (KBr) 1707 cm−; 1H-NMR (DMSO-d6) δ 1.02–1.12 (m, 3 H), 2.25 (s, 3 H), 2.50 (s, 2 H), 3.35–3.89 (m, 10 H), 4.11–4.16 (m, 2H), 6.71–8.56 (series of m, total 12H), 12.65 (br s, 1H); MS (FAB) m/z 536 (M30 +1); Anal. Calcd for C29H33N3O7.3/4H2O: C, 63.43; H, 6.33; N, 7.65. Found: 63.34; H, 6.28; N, 7.28.

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