N-Iodosuccinimide → HCID 24773447, Verbindung

HRID 646516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646516
[CH2:1]([NH:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:13][C:12]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:8][N:7]=1)=[O:5])[CH3:2].[I:37]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([I:37])=[C:9]([C:11]2[CH:16]=[C:15]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:13][C:12]=2[O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:8][N:7]=1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 247733585-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

Produkt 1

HCID 24773447HCID 24773447, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-isoxazole-3-carboxylic acid ethylamide (1 eq) and N-iodosuccinimide (2.0 eq), were dissolved in acetonitrile, ceric ammonium nitrate (0.1 eq) added and the solution was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the resulting gum was partitioned between ethyl acetate and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography, eluting with 4:1 hexane:ethyl acetate, to give 5-(2,4-bis-benzyloxy-5-isobutyl-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamide as an oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting gum was partitioned between ethyl acetate and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with 4:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-6ecdad9bde3a41b49591ea2d9cb158ba
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705027B2

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