1-Hydroxybenzotriazole → HCID 69334014, compound

Participants

Reaction Steps

To a solution of 4-[N′-(2-benzyloxyphenyl)ureido]-3-methoxyphenylacetic acid (1.12 g, 2.76 mmol), methyl 4-(2-pyrrolidinylmethoxy)-3-nitrobenzoate (890 mg, 2.76 mmol), HOBt (74.0 mg, 0.55 mmol), DMAP (67.0 mg, 0.55 mmol), and Et3 N (0.58 mL, 4.13 mmol) in THF (15 mL) was added EDC.HCl (792 mg, 4.13 mmol). After being stirred at room temperature for 12 hr, the reaction mixture was diluted with water and extracted with EtOAc. The extracts were washed with brine, dried over Na2SO4, and concentrated to dryness. Chromatography of the residue with EtOAc as eluent gave methyl 4-[1-[4-[N′-(2-benzyloxyphenyl)ureido]-3-methoxyphenylacetamido ]-2-pyrrolidinylmethoxy]-3-nitrobenzoate (1.52 g, 82%) as a yellow amorphous solid. 1H-NMR (CDCl3) δ 1.91 (m, 1H), 1.95–2.17 (m, 3H), 3.47–3.53 (m, 2H), 3.56 (s, 2H), 3.60 (m, 1H), 3.68 (s, 3H), 3.90 (s, 3H), 4.11 (d, J=7.3 Hz, 1 H), 4.45 (m, 1H), 5.08 (s, 2H), 6.70 (dd, J=8.3, 1.9 Hz, 1H), 6.75 (d, J=1.9 Hz, 1H), 6.91–6.99 (m, 31H), 7.16 (s, 1H), 7.18 (d, J=8.3 Hz, 1H), 7.33–7.40 (m, 6H), 7.91 (d, J=8.3 Hz, 1H), 8.11–8.16 (m, 2H), 8.46 (s, 1H).

Provenance & Evidence