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Triethylamine → HCID 18758355、化合物

HRID 1661777
ノート
印刷プレビュー

反応式

HRID 1661777 の反応式
Cl.[NH2:2][CH:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][CH3:19])[CH:10]=1)[CH2:4][CH:5]([OH:8])[CH2:6][CH3:7].[C:20]([NH:23][C:24]1[CH:34]=[CH:33][CH:32]=[C:26]2[C:27]([O:29][C:30](=O)[C:25]=12)=[O:28])(=[O:22])[CH3:21].C(N(CC)CC)C>CN(C=O)C>[CH2:18]([O:17][C:11]1[CH:10]=[C:9]([CH:3]([N:2]2[C:30](=[O:29])[C:25]3[C:26](=[CH:32][CH:33]=[CH:34][C:24]=3[NH:23][C:20](=[O:22])[CH3:21])[C:27]2=[O:28])[CH2:4][CH:5]([OH:8])[CH2:6][CH3:7])[CH:14]=[CH:13][C:12]=1[O:15][CH3:16])[CH3:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2261213-Acetamidophthalic AnhydrideHCID 67429816HCID 67429816、化合物

生成物 1

HCID 18758355HCID 18758355、化合物収率 77.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A stirred mixture of 5-amino-5-(3-ethoxy-4-methoxyphenyl)pentan-3-ol hydrochloride (1.15 g, 3.97 mmol), 3-acetamidophthalic anhydride (0.82 g, 3.97 mmol) and triethylamine (0.4 g, 3.97 mmol) in DMF (20 mL) was heated at 80-90° C. for 6 hours. The mixture was then concentrated in vacuo. The residue was dissolved in ethyl acetate (80 mL), washed with water (30 mL), brine (30 mL) and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified by chromatography (Silica gel, methylene chloride:ethyl acetate 8:2) to give N-{2-[1-(3-ethoxy-4-methoxyphenyl)-3-hydroxypentyl]-1,3-dioxoisoindolin-4-yl}acetamide (1.35 g, 77%); 1H NMR (CDCl3) δ 9.52 (s, 1H), 8.71 (d, J=8.4 Hz, 1H), 7.63 (t, J=7.6 Hz, 1H), 7.48 (d, J=7.3 Hz, 1H), 7.09-7.07 (m, 2H), 6.83-6.80 (m, 1H), 5.61-5.55 (J=3.9, 11.9 Hz, 1H), 4.11 (q, J=6.9 Hz, 2H), 3.84 (s, 3H), 3.47 (m, 1H), 2.97-2.86 (m, 1H), 2.25 (s, 3H), 2.06-1.95 (m, 1H), 1.78 (b, 1H), 1.62-1.52 (m, 2H), 1.45 (t, J=7.0 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H); 13C NMR (CDCl3) δ 170.39, 169.23, 168.11, 148.94, 148.14, 137.32, 135.83, 131.81, 131.19, 124.72, 120.30, 117.94, 115.31, 112.87, 111.09, 70.01, 64.36, 55.86, 51.29, 37.92, 30.46, 24.92, 14.73, 9.90.

後処理

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (80 mL)
  3. washwashed with water (30 mL), brine (30 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by chromatography (Silica gel, methylene chloride:ethyl acetate 8:2)

出典と根拠

ORDレコード
ord-b191936359be41309a8756da7d1d72bb
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030343B2

反応ノート

読み込み中…

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