Trifluoroacetic acid → HCID 70048063, Verbindung

HRID 1197929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197929
[CH:1]1([CH2:7][C@H:8]([NH:18]C(=O)OC(C)(C)C)[C@@H:9]([OH:17])[CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl>[NH2:18][C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C@@H:9]([OH:17])[CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 86747488HCID 86747488, Verbindung

Produkt 1

HCID 70048063HCID 70048063, VerbindungAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.41 g (1.16 mmol) of t-butyl [(1S,2S)-1-(cyclohexylmethyl)-2-hydroxy-3-(2-oxo-1-pyrrolidinyl)propyl]carbamate was dissolved in 5 ml of methylene chloride, treated at 0° with 1.5 ml of 90% trifluoroacetic acid and subsequently stirred at room temperature for 5 hours. Thereafter, the reaction mixture was slowly added dropwise to 2N sodium carbonate solution, subsequently treated with 3N sodium hydroxide solution and finally extracted with methylene chloride. The methylene chloride extracts were dried over potassium carbonate and evaporated under reduced pressure, whereby there were obtained 249 mg of 1-[(2S,3S)-3-amino4-cyclohexyl-2-hydroxybutyl]-2-pyrrolidinone as an oil, MS: 255 (M+H)+.

Aufarbeitung

  1. extractionfinally extracted with methylene chloride
  2. dry with materialThe methylene chloride extracts were dried over potassium carbonate
  3. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-146e9cf388f548f89ce69fa31b7941ea
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05278148

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