Anisole → N-(2-benzoylphenyl)tyrosine methyl ester

HRID 1358579노트

반응식

HRID 1358579 반응식
Cl.[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[NH2:6].[C:16]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C:25]1=O)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(OC)C=CC=CC=1>[Pd].C(N(CC)CC)C>[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[NH:6][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16](=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

6

반응물 3

HCID 7519AnisoleHCID 76956Methyl tyrosinate hydrochlorideHCID 2756272-Benzoylcyclohexanone

생성물 1

HCID 10667178N-(2-benzoylphenyl)tyrosine methyl ester

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8471Triethylamine용매

실험 절차

A mixture of tyrosine methyl ester hydrochloride (4.8 g), 2-benzoylcyclohexanone (5.0 g), palladium on carbon (1.0 g, 10%), triethylamine (2.9 ml) and anisole (70 ml) was heated at reflux for 20 hours. The reaction mixture was filtered and the filtrate was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane: ethyl acetate=3:1 as the eluant to afford the title compound (1.83 g, Rf=0.39: thin layer chromatography on a silica gel plate using hexane: ethyl acetate=3:1 as the eluant).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was partitioned between ethyl acetate and water
  5. washThe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on a silica gel column

출처 및 근거

ORD 기록
ord-75e3047c14394a13a12f2857ab425ecd
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596751B2

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