Hydroxyphenylacetic acid → Pterostilbene

HRID 2406867

반응식

HRID 2406867 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=O.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1.Cl>C(OC(=O)C)(=O)C.C(N(CC)CC)C.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:5](/[CH:6]=[CH:20]/[C:17]2[CH:16]=[CH:15][C:14]([OH:13])=[CH:19][CH:18]=2)[CH:4]=1.[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:6]=[C:20](/[C:17]2[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][CH:16]=2)\[C:21]([OH:23])=[O:22])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

참가 물질

8

반응물 3

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 817473,5-Dimethoxybenzaldehyde

생성물 2

HCID 5281727PterostilbeneHCID 5386532Z-3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acid

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 7918Acetic Anhydride용매HCID 8471Triethylamine용매

반응 조건

온도
150 °C

실험 절차

Pterostilbene (trans-3,5-dimethoxy-4′-hydroxystilbene) was synthesized (as modified from Pettit et al., 1988, J. Nat. Prod. 51:517-527) by condensation of 3,5-dimethoxybenzaldehyde and 4-hydroxyphenylacetic acid in acetic anhydride and triethylamine. The reaction mixture was heated (150° C.) under an atmosphere of nitrogen, and continuously stirred. After 20 hours, the reaction was stopped, cooled to room temperature, and concentrated hydrochloric acid (5 mL) was added. The formed precipitate was dissolved in 50 mL chloroform and extracted with 10% aqueous sodium hydroxide. The aqueous extract was acidified to pH 1 with concentrated hydrochloric acid, and stirred for at least 6 hours, resulting in the precipitation of the intermediate product, α-[(3,5-dimethoxyphenyl)methylene]-4-hydroxy-(αZ)-benzeneacetic acid. This intermediate product was heated with 1.0 g of copper in 10 mL quinoline (200° C., 6 hours, under nitrogen). The reaction mixture was cooled to room temperature and filtered. 5 N hydrochloric acid (25 mL) was added to filtrate, stirred for 1 hour, and extracted with chloroform. The chloroform extract containing impure pterostilbene was purified by flash chromatography on a Horizon HPFC system (Biotage, Inc., Charlottesville, Va.), using silica gel column, and solvent system ethyl acetate:hexane (linear gradient from 15:85 to 100% ethyl acetate). Fractions containing pure pterostilbene were combined and concentrated in vacuum. Pterostilbene was recrystallized in hexane, and its structure confirmed from its spectroscopic data (UV, mass spectrometry, and nuclear magnetic resonance spectroscopy).

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with 10% aqueous sodium hydroxide
  3. extractionThe aqueous extract
  4. stirringstirred for at least 6 hours

출처 및 근거

ORD 기록
ord-e158f752443c47928785a3e7d8cb5af4
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809400B2

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