Sodium Hydroxide → HCID 23512019, compound

Participants

Reaction Steps

To a stirred solution of ethyl 3-methoxy-4-(2-aminoethoxy)benzoate (250 mg, 1.04 mmol) and pentafluorophenyl ester of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (500 mg, 1.04 mmol) was added Et3 N (210 μl, 3.01 mmol), and the resulting mixture was stirred for 2 days. 0.25 N NaOH (20 mL) and THF (20 mL) was added to the mixture and the resulting mixture was heated under reflux overnight. After cooling, the mixture was evaporated and the residue was acidified by the addition of 1 N HCl. The mixture was extracted with CHCl3, and the extract was washed with brine, dried over Na2SO4, and evaporated. The obtained crude solid was recrystallized from CHCl3 to give 110 mg (20% for 2 steps ) 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]aminoethoxy]benzoic acid 255 as a white crystalline powder. mp 180–181° C.; IR (KBr) 1687 cm−1; 1H-NMR (DMSO-d6) δ 2.24 (s, 3 H), 3.37 (s, 2 H), 3.38 (s, 2 H), 3.41–3.50 (m, 2 H), 3.81 (s, 3 H), 3.83 (s, 3 H), 4.06–4.08 (m, 2 H), 6.76–8.55 (series of m, total 12 H); MS (FAB) m/z 508 (M++1); Anal. Calcd for C27H29N3O7.1/2H2O: C, 62.78; H, 5.85; N, 8.13. Found: C, 62.46; H, 5.69; N, 8.03.

Provenance & Evidence