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O-Xylene → N-(5-(1-(4-Acetoxytetrahydrofuran-3-yloxycarbonyl)ethylamino)-4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1653965
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1653965
[NH2:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([F:19])=[C:6]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])[CH:7]=1.Br[CH:22]([CH3:35])[C:23]([O:25][CH:26]1[CH:30]([O:31][C:32](=[O:34])[CH3:33])[CH2:29][O:28][CH2:27]1)=[O:24].C(=O)([O-])O.[Na+].C1(C)C(C)=CC=CC=1>C(OCC)(=O)C>[C:32]([O:31][CH:30]1[CH2:29][O:28][CH2:27][CH:26]1[O:25][C:23]([CH:22]([NH:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([F:19])=[C:6]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])[CH:7]=1)[CH3:35])=[O:24])(=[O:34])[CH3:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7237O-XyleneHCID 516892Sodium BicarbonateHCID 15590180N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimideHCID 200789494-Acetoxytetrahydrofuran-3-yl 2-bromopropionate

Produkt 1

HCID 20078935N-(5-(1-(4-Acetoxytetrahydrofuran-3-yloxycarbonyl)ethylamino)-4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide
Ausbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 8.84 g of N-(5-amino-4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide, 12.6 g of 4-acetoxytetrahydrofuran-3-yl 2-bromopropionate, 3.02 g of sodium hydrogencarbonate and 3 ml of xylene was heated under stirring at 150° to 160 ° C. for 4 hours. Adding ethyl acetate to the reaction mixture while it remained warm, the resulting mixture was washed with water, subsequently with aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by chromatography on a silica gel column (development solvent: ethyl acetate/hexane=1/2), to obtain 4.88 g of a compound described in Table 1 (No. 10) (33%).

Aufarbeitung

  1. temperaturewas heated
  2. washthe resulting mixture was washed with water, subsequently with aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe residue was purified by chromatography on a silica gel column (development solvent: ethyl acetate/hexane=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-653fee0bc36d4b6ba4be69ed5419edd7
Quelldatensatz
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05405828

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