Water → 3-(4-Ethoxy-2-oxocyclohex-3-enyl)propyl 2-(methylamino)benzoate

HRID 77270

反応式

HRID 77270 の反応式
[CH2:1]([O:3][C:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH2:12][OH:13])[C:6](=[O:14])[CH:5]=1)[CH3:2].CCN(CC)CC.[CH3:22][N:23]1C(=O)O[C:26](=[O:27])[C:25]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:24]12.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:22][NH:23][C:24]1[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=1[C:26]([O:13][CH2:12][CH2:11][CH2:10][CH:7]1[CH2:8][CH2:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]1=[O:14])=[O:27]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 25160N-Methylisatoic anhydrideHCID 252417513-Ethoxy-6-(3-hydroxypropyl)cyclohex-2-enone

生成物 1

HCID 252417523-(4-Ethoxy-2-oxocyclohex-3-enyl)propyl 2-(methylamino)benzoate収率 45%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

Alcohol 3 (180 mg, 0.89 mmol), NEt3 (0.56 mL) and catalytic DMAP were added to a solution of N-methylisatoic anhydride (220 mg, 0.89 mmol) in dry DMF (2.0 mL) at rt. After stirring overnight, the solution was warmed to 65° C. for 3 h. After cooling to rt, water was added and this mixture was extracted with ethyl acetate (5×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated to give the crude product, which was purified by flash column chromatography to afford 87.0 mg (45% yield) of 4 as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.85 (1H, m), 7.33 (1H, m), 6.56 (2H, m), 5.27 (1H, s), 4.22 (2H, t, J=5.2 Hz), 3.85 (2H, q, J=7.0 Hz), 2.86 (3H, s), 2.39 (2H, t, J=5.3 Hz), 2.04-1.41 (7H, m), 1.31 (3H, t, J=7.0 Hz); 13C NMR (75 MHz, CDCl3) δ 201.1, 176.8, 168.7, 151.7, 134.7, 131.7, 115.0, 111.3, 110.6, 102.5, 101.9, 64.7, 64.5, 64.3, 44.9, 30.0, 28.2, 26.6, 26.5, 26.4, 14.3; ESI MS m/z 354 (M++Na+).

後処理

  1. temperatureAfter cooling to rt
  2. extractionthis mixture was extracted with ethyl acetate (5×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product, which
  8. customwas purified by flash column chromatography

出典と根拠

ORDレコード
ord-958ff28899cb4cf1895dc65cd340913b
出典データセット
uspto-grants-2014_09
特許番号
US08841132B2

関連ノート

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