Hydrofluoric Acid → HCID 86747488, Verbindung

HRID 1197928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197928
[O:1]([C@@H:9]([CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32])[C@@H:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[Si](C(C)(C)C)(C)C.F.C(=O)(O)[O-].[Na+]>C(#N)C>[CH:12]1([CH2:11][C@H:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[C@@H:9]([OH:1])[CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][C:28]2=[O:32])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Komponenten

6

Edukt 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 57180353HCID 57180353, Verbindung

Produkt 1

HCID 86747488HCID 86747488, VerbindungAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 178435178HCID 178435178, VerbindungLösungsmittel

Versuchsvorschrift

0.62 g (1.28 mmol) of t-butyl [(1S,2S)-2-(t-butyldimethylsiloxy)-1-(cyclohexylmethyl)-3-(2-oxo-1-pyrrolidinyl)propyl]carbamate was dissolved in 9 ml of acetonitrile in a polypropylene reaction vessel and treated at room temperature with 1.2 ml of 40% aqueous hydrofluoric acid. The reaction mixture was subsequently stirred at room temperature for 3 hours, thereafter poured into 2N sodium bicarbonate solution and extracted with methylene chloride. The methylene chloride extracts were dried over magnesium sulfate and evaporated under reduced pressure, whereby there were obtained 434 mg of t-butyl [(1S,2S)-1-(cyclohexylmethyl)-2-hydroxy-3-(2-oxo-1-pyrrolidinyl)propyl]carbamate as an oil which was used directly in the next step.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. dry with materialThe methylene chloride extracts were dried over magnesium sulfate
  3. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-589e8dbc24544d2e864d7e65a7cdec62
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05278148

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