تفاعل #9939

معادلة التفاعل

N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)-propionamide

ethyl acetate

→

3-(4-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide

المردود 102.0%

المذيبات

ethyl acetate methanol tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   ترشيحAfter 24 hours the suspension was filtered through a pad of Celite
2. 2
   غسيلwas washed with methanol (30 mL) and methylene chloride (30 mL)
3. 3
   تركيزThe filtrate was concentrated in vacuo
4. 4
   أخرىto give an oil

الإجراء التجريبي

A mixture of N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)-propionamide (2.3 g, 4.42 mmol) and Pd(OH)2/C (600 mg) in ethyl acetate/methanol/tetrahydrofuran (150 mL each) was shaken under hydrogen. After 24 hours the suspension was filtered through a pad of Celite, and then was washed with methanol (30 mL) and methylene chloride (30 mL). The filtrate was concentrated in vacuo to give an oil. The oil was stirred with ethyl acetate (10 mL) to afford 3-(4-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide as a yellow solid (1.8 g, 100% yield): mp, 193.0–195.0° C.; 1H NMR (DMSO-d6) δ 1.31 (t, J=6.9 Hz, 3H, CH3), 3.05 (d, J=7.9 Hz, 2H, CH2), 3.71 (s, 3H, CH3), 3.96 (q, J=7.0 Hz, 2H, CH2), 5.57 (t, J=7.9 Hz, 1H, NCH), 6.47 (br s, 2H, NH2), 6.77 (dd, J=2.0, 8.3 Hz, 1H, Ar), 6.83–6.88 (m, 3H, Ar), 6.99 (br s, 1H, Ar), 7.45 (d, J=8.3 Hz, 1H, Ar), 8.78 (br s, 1H, OH), 10.55 (1H, NH); 13C NMR (DMSO-d6) δ 14.69, 34.51, 49.75, 55.45, 63.73, 106.82, 111.74, 112.38, 116.32, 116.73, 119.60, 124.89, 131.85, 134.18, 147.62, 148.42, 155.00, 166.111, 167.70, 168.00; Anal Calcd for C20H21N3O6: C, 60.14; H, 5.30; N, 10.52. -Found: C, 60.00; H, 5.34; N, 10.30.

المصدر