p-Toluenesulfonic acid → N-(4-ethylphenyl)alanine Methyl Ester

HRID 23044

反応式

HRID 23044 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[C:11]([O:16][CH3:17])(=[O:15])[C:12]([CH3:14])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H]>C(O)C.[Pd]>[CH3:17][O:16][C:11](=[O:15])[C@H:12]([CH3:14])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 7468p-AminoacetophenoneHCID 11748Methyl pyruvateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 54481932N-(4-ethylphenyl)alanine Methyl Ester

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of 0.68 g (5 mmol) of 4′-aminoacetophenone (Aldrich), 0.60 mL of 90% methyl pyruvate (Aldrich) and 0.05 g (0.25 mmol) of p-toluenesulfonic acid in ethanol was hydrogenated in the presence of a catalytic amount of 10% Pd/C at from 30 to 15 psi of hydrogen for 16 hours. The catalyst was removed by filtering the reaction mixture through Celite and the solvent was evaporated to provide the crude product. The product was purified by column chromatography (silica gel using 1:9 EtOAc/hexanes as the eluant) to provide the title compound.

後処理

  1. customThe catalyst was removed
  2. filtrationby filtering the reaction mixture through Celite
  3. customthe solvent was evaporated
  4. customto provide the crude product
  5. customThe product was purified by column chromatography (silica gel using 1:9 EtOAc/hexanes as the eluant)

出典と根拠

ORDレコード
ord-312cc757e64f4117a954353b5e58fa69
出典データセット
uspto-grants-2005_02
特許番号
US06849650B2

関連ノート

読み込み中…