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

HRID 23044

반응식

HRID 23044 반응식
[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

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 7468p-AminoacetophenoneHCID 11748Methyl pyruvateHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-312cc757e64f4117a954353b5e58fa69
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849650B2

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