Tyrosine Methyl Ester → 2-[1-Methyl-3-oxo-3-(3-pyridyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl ester

HRID 916143

反応式

HRID 916143 の反応式
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[NH2:5].[C:15]([CH2:23][C:24]([CH3:26])=O)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1>CO>[CH3:1][O:2][C:3](=[O:14])[CH:4]([NH:5][C:24]([CH3:26])=[CH:23][C:15](=[O:22])[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 70652Tyrosine Methyl EsterHCID 3001601-(Pyridin-3-yl)butane-1,3-dione

生成物 1

HCID 671332772-[1-Methyl-3-oxo-3-(3-pyridyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl ester収率 79%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of L-tyrosine methyl ester (4.00 g, 20.51 mmol) in methanol (150 ml) is added 1-nicotinoylacetone (3.68 g, 22.56 mmol), then the mixture is heated to reflux for 24 h. The solvent is evaporated under a vacuum. To the residue is added ethanol (50 ml), then the ethanol is distilled off under atmospheric pressure. The crude product is purified by silica gel chromatography using hexane/EtOAc (4:1) as eluent to give the title compound (5.51 g, 79%).

後処理

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 24 h
  3. customThe solvent is evaporated under a vacuum
  4. additionTo the residue is added ethanol (50 ml)
  5. distillationthe ethanol is distilled off under atmospheric pressure
  6. customThe crude product is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-bf7a318a47654e2ea5f2443c575677bc
出典データセット
uspto-grants-2007_09
特許番号
US07268157B2

関連ノート

読み込み中…