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

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Reaction Steps

To a stirred solution of ethyl 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate (160 mg, 0.28 mmol) in THF (5 mL) was added 0.25 N NaOH (5 mL) and the resulting mixture was the heated under reflux overnight. The mixture was poured into 1 N HCl and the solid was collected. The crude solid was recrystallized from EtOH—CHCl3-n-hexane to give 70 mg (46%) 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoic acid 258 as a yellow crystalline powder. mp 105-110° C.; IR (KBr) 1687 cm−1; 1H-NMR (DMSO-d6) d 1.00-1.10 (m, 3 H), 2.48 (s, 2H), 3.35-381 (m, 10 H), 4.13-4.14 (m, 2 H), 6.70-9.15 (series of m, 12 H); MS (FAB) m/z 540 (M++1); Anal. Calcd. for C28H30FN3O7.1/2H2O: C, 61.31; H, 5.82; N, 7.47. Found: C, 61.05; H, 5.82; N, 7.47.

Provenance & Evidence