Acetic Acid → (Z)-Methyl 3-(2,4-dimethoxyphenyl)-3-((2-ethoxy-2-oxoethyl)amino)acrylate

HRID 75556

反応式

HRID 75556 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11](=O)[CH2:12][C:13]([O:15][CH3:16])=[O:14].Cl.[CH3:19][O:20][C:21](=[O:24])[CH2:22][NH2:23].[C:25](O)(=O)C.C(N(CC)CC)C>CCO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1/[C:11](/[NH:23][CH2:22][C:21]([O:20][CH2:19][CH3:25])=[O:24])=[CH:12]/[C:13]([O:15][CH3:16])=[O:14]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 2063901Methyl 2,4-dimethoxy-beta-oxobenzenepropanoate

生成物 1

HCID 86684695(Z)-Methyl 3-(2,4-dimethoxyphenyl)-3-((2-ethoxy-2-oxoethyl)amino)acrylate収率 69.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

To a solution of methyl 3-(2,4-dimethoxyphenyl)-3-oxopropanoate (5.0 g, 21 mmol) in EtOH (30 mL) was added glycine methyl ester hydrochloride (10.5 g, 83.9 mmol) followed by acetic acid (1.20 mL, 21 mmol) and triethylamine (8.5 g, 83.9 mmol) and the reaction mixture was heated at 100° C. for 18 hours. After cooling to room temperature, the residue was partitioned between EtOAc and saturated aqueous ammonium chloride. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was dissolved in CH2Cl2 (10 mL) filtered through a plug of silica gel, eluting with 15-35% EtOAc in heptanes and dried under vacuum to give the title compound (4.7 g, 69%) as a yellow solid. This material was used in the next step without further purification.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe residue was partitioned between EtOAc and saturated aqueous ammonium chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude product was dissolved in CH2Cl2 (10 mL)
  7. filtrationfiltered through a plug of silica gel
  8. washeluting with 15-35% EtOAc in heptanes
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-9921a0d60d1748beb999e57d661a0712
出典データセット
uspto-grants-2014_09
特許番号
US08835449B2

関連ノート

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