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Water → 7-[3-[4-(Carbomethoxymethoxy)phenethylamino]-2-hydroxypropoxy]flavone Maleate

HRID 478082
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 478082
[OH:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][CH2:7][NH:8][CH2:9][CH:10]([OH:30])[CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:29])[CH:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[O:20]3)=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38].[OH2:41]>CN(C=O)C>[C:19]([OH:41])(=[O:20])/[CH:23]=[CH:36]\[C:37]([OH:39])=[O:38].[C:37]([CH2:36][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][CH2:9][CH:10]([OH:30])[CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:29])[CH:18]=[C:19]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[O:20]3)=[CH:15][CH:14]=2)=[CH:31][CH:32]=1)([O:39][CH3:40])=[O:38]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 14626316HCID 14626316, Verbindung

Produkt 1

HCID 146263197-[3-[4-(Carbomethoxymethoxy)phenethylamino]-2-hydroxypropoxy]flavone MaleateAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

7-[3-[(4-Hydroxyphenethyl)amino]-2-hydroxypropoxy]flavone (10.8 g, 25.1 mmol), Example 13, was dissolved in 20 ml of warm DMF at 50°-60° C. and then cooled to -20° C. Sodium hydride (1.2 g, 0.0251 mmol) was added portionwise to the above cooled solution, stirred at -20° C. for 1 hour, and then cooled to -40° C. Methyl bromoacetate (3.8 g, 25.1 mmol) was added dropwise to the stirred solution and the reaction mixture was kept at this temperature for 2 hours and at RT overnight. The reaction was poured into 1.5 l of water, the water decanted, and the residue washed with two portions of water. The gummy material was then purified by flash column chromatography, eluting with CHCl3 --MeOH (20:1). The isolated material (2.7 g) was recrystallized from methanol, and the crystallized solid was treated with 30 ml of ethanol and maleic acid (0.3 g) to give the title compound as white crystals, mp 154°-156° C., 1.5 g (10% yield).

Aufarbeitung

  1. temperaturecooled to -40° C
  2. waitthe reaction mixture was kept at this temperature for 2 hours and at RT overnight
  3. customthe water decanted
  4. washthe residue washed with two portions of water
  5. customThe gummy material was then purified by flash column chromatography
  6. washeluting with CHCl3 --MeOH (20:1)
  7. customThe isolated material (2.7 g) was recrystallized from methanol
  8. additionthe crystallized solid was treated with 30 ml of ethanol and maleic acid (0.3 g)

Quellen und Nachweise

ORD-Eintrag
ord-dc6241a72ce440c2b3f8362577e595a0
Quelldatensatz
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04889941

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