Urea → HCID 10217675, Verbindung

HRID 2253270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2253270
[NH2:1][C:2]([NH2:4])=[O:3].[O-]CC.[Na+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH2:19][CH:20]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][C:39](OCC)=[O:40])=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)[C:21]([OH:23])=[O:22])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1>C(O)C>[CH3:18][O:17][C:15]1[CH:14]=[C:13]([CH2:19][CH:20]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[CH:33][C:34]([CH2:37][CH2:38][C:39](=[O:40])[NH:1][C:2]([NH2:4])=[O:3])=[CH:35][CH:36]=3)=[CH:26][CH:25]=2)[C:21]([OH:23])=[O:22])[CH:12]=[C:11]([O:10][CH3:9])[CH:16]=1

Komponenten

5

Edukt 3

HCID 1176UreaHCID 2723922Sodium ethoxideHCID 59645405HCID 59645405, Verbindung

Produkt 1

HCID 10217675HCID 10217675, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3-(3,5-Dimethoxyphenyl)-2-{4-[4-(2-ethoxycarbonylvinyl)-phenoxy]-phenyl}-acrylic acid (4, 2.37 g, 5.0 mmol) was dissolved in a mixture of ethanol-dioxane (2:1, 150 mL), and palladium charcoal (10%, 500 mg) was added. The mixture was stirred under hydrogen for 15 hr. Catalyst was then removed by filtration, and solvent was evaporated under reduced pressure to yield 3-(3,5-dimethoxy-phenyl)-2-{4-[4-(2-ethoxycarbonylethyl)-phenoxy]-phenyl}-propionic acid (18) quantitatively. Urea (0.21 g, 3.58 mmol) was dissolved in sodium ethoxide (2.7 M, 2.2 mL, 5.92 mmol) at 80° C. under argon, and to this a solution of 18 (1.13 g, 2.37 mmol) in anhydrous ethanol (15 mL) was added and heated at this temperature for 13 hr. Ethanol was evaporated under reduced pressure, water (20 mL) was added, acidified to pH 1 by 5% aqueous HCl and extracted with ethyl acetate (50 mL). The organic layer was washed with water (2×25 mL), brine (2×20 mL), dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by silica gel chromatography and eluted with hexane-ethyl acetate (3:7) containing acetic acid (1%), followed by recrystallization from ethanol. Yield: 256 mg, 22.8%.

Aufarbeitung

  1. temperatureheated at this temperature for 13 hr
  2. customEthanol was evaporated under reduced pressure, water (20 mL)
  3. additionwas added
  4. extractionextracted with ethyl acetate (50 mL)
  5. washThe organic layer was washed with water (2×25 mL), brine (2×20 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluted with hexane-ethyl acetate (3:7)
  10. additioncontaining acetic acid (1%)
  11. customfollowed by recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-06c9463ed87c4947822993f05f6b1230
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323496B2

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