반응 #9943

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

ether

→

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

수율 64.1%

용매

ethyl acetate methanol

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후처리

1. 1
   여과the suspension was filtered through a pad of Celite
2. 2
   세척the pad washed with methanol (75 mL) and methylene chloride (75 mL)
3. 3
   농축The filtrate was concentrated in vacuo
4. 4
   기타to give an oil

실험 절차

A mixture of N-benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(3-nitrophthalimido)-propionamide (1.32 g, 2.54 mmol) and 10% Pd/C (230 mg) in ethyl acetate/methanol (150 mL each) was shaken under 50–60 psi of H2. After 3 days, the suspension was filtered through a pad of Celite, and the pad washed with methanol (75 mL) and methylene chloride (75 mL). The filtrate was concentrated in vacuo to give an oil. The oil was stirred with ether (20 mL) to afford 3-(3-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxypropionamide as a yellow solid (650 mg, 64% yield): mp, 143.0–145.0° C.; 1H NMR (DMSO-d6) δ 1.39 (t, J=6.9 Hz, 3H, CH3), 3.16 (d, J=7.8 Hz, 2H, CH2), 3.79 (s, 3H, CH3), 4.05 (q, J=6.9 Hz, 2H, CH2), 5.68 (t, J=7.8 Hz, 1H, NCH), 6.55 (br s, 2H, NH2), 6.98–7.08 (m, 5H, Ar), 7.47–7.53 (m, 1H, Ar), 8.88 (br s, 1H, OH), 10.66 (1H, NH); 13C NMR (DMSO-d6) δ 14.70, 34.37, 49.65, 55.47, 63.75, 108.64, 110.68, 111.77, 112.39, 119.61, 121.40, 131.69, 132.03, 135.19, 146.48, 147.65, 148.47, 166.14, 167.81, 169.18; Anal Calcd for C20H21N3O6: C, 60.14; H, 5.30; N, 10.52. Found: C, 59.76; H, 5.21; N, 10.30.

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