Trifluoromethanesulfonic anhydride → 6-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl Trifluoromethanesulfonate

HRID 480445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 480445
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[OH:16][C:17]([C:45]1[CH:46]=[C:47]2[C:52](=[CH:53][CH:54]=1)[CH:51]=[C:50](O)[CH:49]=[CH:48]2)([C:21]1[N:22]=[CH:23][N:24]([C:26]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=1)[CH:18]([CH3:20])[CH3:19]>N1C=CC=CC=1.O>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:50]1[CH:49]=[CH:48][C:47]2[C:52](=[CH:53][CH:54]=[C:45]([C:17]([OH:16])([C:21]3[N:22]=[CH:23][N:24]([C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:25]=3)[CH:18]([CH3:19])[CH3:20])[CH:46]=2)[CH:51]=1)(=[O:5])=[O:4]

Komponenten

5

Edukt 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 220183856-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthol

Produkt 1

HCID 222850556-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl Trifluoromethanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (9.1 mL) was added dropwise to a solution of 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthol (27.0 g) in pyridine (200 mL) at 0° C. The reaction mixture was stirred for 1 h at 0° C., diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate=1:1). Crystallization from diisopropyl ether gave the titled compound (29.6 g) as a colorless powder.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate=1:1)
  6. customCrystallization from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-572bb105840e4666833adeae9b41221f
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06649643B1

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