Hexane → 3-(3-Ethoxy-4-methoxyphenyl)-3-(4-methylphthalimido)propanoic acid

HRID 9827

反応式

HRID 9827 の反応式
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH2:16][CH3:17])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH3:18][C:19]1[CH:20]=[C:21]2[C:26](=O)[O:25][C:23](=[O:24])[C:22]2=[CH:28][CH:29]=1.C(OCC)(=O)C.CCCCCC>C(O)(=O)C.O>[CH2:16]([O:15][C:9]1[CH:8]=[C:7]([CH:2]([N:1]2[C:26](=[O:25])[C:21]3=[CH:20][C:19]([CH3:18])=[CH:29][CH:28]=[C:22]3[C:23]2=[O:24])[CH2:3][C:4]([OH:6])=[O:5])[CH:12]=[CH:11][C:10]=1[O:13][CH3:14])[CH3:17]

参加物

7

反応物 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 880694-Methylphthalic anhydrideHCID 41021513-Amino-3-(3-ethoxy-4-methoxyphenyl)propanoic acid

生成物 1

HCID 219886643-(3-Ethoxy-4-methoxyphenyl)-3-(4-methylphthalimido)propanoic acid収率 71%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

A stirred solution of 3-amino-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (3.00 g, 12.5 mmol) and 4-methylphthalic anhydride (2.13 g, 12.5 mmol, 95%) in acetic acid was heated to reflux under nitrogen for 18 hours. The mixture was allowed to cool to room temperature. The solvent was removed in vacuo to give an oil. The resulting oil was stirred with ethyl acetate (10 mL), hexane (10 mL) and water (30 mL) for 30 minutes. The resulting suspension was filtered. The solid was washed with water (3×10 mL) and hexane (3×10 mL), and then was dried in a vacuum oven overnight (60 ° C., <1 torr) to give 3-(3-ethoxy-4-methoxyphenyl)-3-(4-methylphthalimido)propanoic acid as a white solid (3.4 g, 71% yield): mp, 134.0–136.0° C.; 1H NMR (DMSO-d6) δ 1.31 (t, J=6.9 Hz, 3H, CH3), 2.47 (s, 3H, CH3), 3.23 (dd, J=6.7, 16.5 Hz, 1H, CHH), 3.50 (dd, J=9.2, 16.5 Hz, 1H, CHH), 3.72 (s, 3H, CH3), 3.97 (q, J=6.9 Hz, 2H, CH2), 5.58 (dd, J=6.7, 9.1 Hz, 1H, NCH), 6.90–6.95 (m, 2H, Ar), 7.01 (br s, 1H, Ar), 7.61–7.76 (m, 3H, Ar), 12.4 (br s, 1H, OH); 13C NMR (DMSO-d6) δ 14.65, 21.32, 36.09, 50.04, 55.45, 63.72, 111.79, 112.15, 119.29, 123.08, 123.58, 128.51, 131.35, 131.49, 134.95, 145.63, 147.75, 148.53, 167.67, 167.78, 171.72; Anal Calcd for C21H21NO6: C, 65.79; H, 5.52; N, 3.65. Found: C, 65.46; H, 5.57; N, 3.31.

後処理

  1. temperatureto reflux under nitrogen for 18 hours
  2. customThe solvent was removed in vacuo
  3. customto give an oil
  4. filtrationThe resulting suspension was filtered
  5. washThe solid was washed with water (3×10 mL) and hexane (3×10 mL)
  6. customwas dried in a vacuum oven overnight (60 ° C., <1 torr)

出典と根拠

ORDレコード
ord-fc860f8e8ab649108b5b56d9f4f04be3
出典データセット
uspto-grants-2006_08
特許番号
US07091356B2

関連ノート

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