Phosphonium, hexyltriphenyl-, bromide (1:1) → HCID 68818416, Verbindung

HRID 732591

Reaktionsgleichung

Reaktionsgleichung von HRID 732591
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].CC(C)([O-])C.[K+].[C:33]([O:37][C:38]([N:40]1[CH2:44][C:43](=O)[CH2:42][C@@H:41]1[C@H:46]1[O:50][C:49]([CH3:52])([CH3:51])[N:48]([C:53](=[O:55])[CH3:54])[C@H:47]1[CH2:56][C:57]1[CH:62]=[C:61]([F:63])[CH:60]=[C:59]([F:64])[CH:58]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>C1COCC1>[C:33]([O:37][C:38]([N:40]1[CH2:44]/[C:43](=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])/[CH2:42][C@@H:41]1[C@H:46]1[O:50][C:49]([CH3:51])([CH3:52])[N:48]([C:53](=[O:55])[CH3:54])[C@H:47]1[CH2:56][C:57]1[CH:58]=[C:59]([F:64])[CH:60]=[C:61]([F:63])[CH:62]=1)=[O:39])([CH3:36])([CH3:34])[CH3:35]

Komponenten

5

Edukt 3

HCID 2724569Phosphonium, hexyltriphenyl-, bromide (1:1)HCID 23665647Potassium tert-butoxideHCID 68814480HCID 68814480, Verbindung

Produkt 1

HCID 68818416HCID 68818416, VerbindungAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Place under argon a suspension of n-hexyltriphenylphosphonium bromide (0.420 g, 1 mmol) in 10 mL of dry THF. Add potassium tert-butoxide (0.112 g, 1 mmol). Stir the mixture for 1 h. Add a solution of (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (0.045 g, 0.1 mmol) in 5 mL of dry THF. Stir the mixture overnight. Add water, extract with diethyl ether, dry over MgSO4, concentrate under reduced pressure and purify (silica gel chromatography, eluting with ethyl ether:hexane mixtures) to give the title compound (0.04 g, 76%).

Aufarbeitung

  1. stirringStir the mixture overnight
  2. extractionAdd water, extract with diethyl ether
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate under reduced pressure
  5. custompurify
  6. wash(silica gel chromatography, eluting with ethyl ether:hexane mixtures)

Quellen und Nachweise

ORD-Eintrag
ord-2818c567f17b4da281a5882559522ab8
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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