Imidazole → 4(r)-Benzyl-3-(2-iodomethyl-3-methylbutyryl)oxazolidin-2-one

HRID 992425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992425
[I:1]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[CH2:27]([C@@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:47])[C@@H:41]([CH2:45]O)[CH:42]([CH3:44])[CH3:43])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[CH2:27]([C@@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:47])[CH:41]([CH2:45][I:1])[CH:42]([CH3:44])[CH3:43])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 228882854-(R)-Benzyl-3-(2-(R)-hydroxymethyl-3-methylbutyryl)oxazolidin-2one

Produkt 1

HCID 228882814(r)-Benzyl-3-(2-iodomethyl-3-methylbutyryl)oxazolidin-2-oneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Iodine (42 g), triphenylphosphine (47 g) and imidazole (12 g) were added to a solution of 4-(R)-benzyl-3-(2-(R)-hydroxymethyl-3-methylbutanoyl)oxazolidin-2-one (45 g) in toluene (400 ml) and the mixture was heated to 80° C. for 1 h, then cooled and washed with water and saturated brine. The solvent was dried (Na2SO4) and evaporated and the residue filtered through silica (200 g) eluting with diethyl ether-hexane 1:1 to give the title compound as a yellow viscous oil (56.4 g).

Aufarbeitung

  1. temperaturecooled
  2. washwashed with water and saturated brine
  3. dry with materialThe solvent was dried (Na2SO4)
  4. customevaporated
  5. filtrationthe residue filtered through silica (200 g)
  6. washeluting with diethyl ether-hexane 1:1

Quellen und Nachweise

ORD-Eintrag
ord-7ab54d8d928649488104a42526c7bc4d
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06469020B2

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