Реакция #437564

Уравнение реакции

4-[4-benzyloxy-1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]-3-methoxybenzoate

AcOH EtOH

→

ethyl 4-[4-hydroxy-1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]-3-methoxybenzoate

Выход 24.0%

Условия реакции

Обработка

1. 1
   ФильтрацияThe mixture was filtered
2. 2
   Другоеto remove the catalyst
3. 3
   Концентрированиеthe filtrate was concentrated in vacuo
4. 4
   ДругоеThe residue was chromatographed on silica-gel with CHCl3:EtOH (10:1

Методика

A stirred mixture of 4-[4-benzyloxy-1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]-3-methoxybenzoate (440 mg, 0.645 mmol) and 5% Pd/C (400 mg) in AcOH:EtOH (1:1, v/v, 100 mL) was hydrogenated at 1 atm for 5 hr. The mixture was filtered to remove the catalyst and the filtrate was concentrated in vacuo. The residue was chromatographed on silica-gel with CHCl3:EtOH (10:1, v/v) as eluent to give 90 mg (24%) ethyl 4-[4-hydroxy-1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]-3-methoxybenzoate as a pale yellow oil. 1H-NMR (CDCl3) δ 1.39 (3 H, t, J=7.3 Hz), 2.04–2.37 (total 5 H, m), 3.44–4.70 (16 H, series of m), 6.63 (1 H, s), 6.70–6.80 (2 H, m), 6.84 (1 H, d, J=8.3 Hz), 7.11 (1H, t, J=7.8 Hz), 7.20–7.24 (3 H, m), 7.45 (1 H, d, J=2.0 Hz), 7.59 (2 H,dd, J=8.3, 2.0 Hz), 8.01 (1 H, d, J=7.8 Hz).

Источник