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Triethylamine → 4-Fluoro-L-proline

HRID 557112
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 557112
[CH2:1]([N:3](CC)[CH2:4][CH3:5])[CH3:2].S(F)([F:11])(=O)=O.[C:13](=[O:16])([O-])[O-:14].[K+].[K+]>C(#N)C>[F:11][CH:5]1[CH2:4][NH:3][C@H:1]([C:13]([OH:14])=[O:16])[CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 11430Potassium Carbonate2×HCID 17607Sulfuryl fluoride

Produkt 1

HCID 222148884-Fluoro-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

10.0 mL of acetonitrile, and 1.10 g (10.87 mmol, 1.09 eq) of triethylamine, followed by lowering the inside temperature to −40° C. and then bubbling 2.00 g (19.60 mmol, 1.96 eq) of sulfuryl fluoride from a cylinder. The inside temperature was returned to room temperature, and stirring was conducted for 20 hours and 20 minutes. Conversion of the reaction was found by gas chromatography measurement to be 100%. The reaction-terminated liquid was poured into a potassium carbonate aqueous solution [prepared from 2.80 g (20.26 mmol, 2.03 eq) of potassium carbonate and 50.0 mL of water], followed by extraction two times with 50.0 mL of ethyl acetate. The recovered organic layer was concentrated under reduced pressure, followed by vacuum drying, thereby obtaining a crude product of 4-fluoroproline derivative represented by the following formula,

Aufarbeitung

  1. customto −40° C.
  2. customwas returned to room temperature
  3. extractionfollowed by extraction two times with 50.0 mL of ethyl acetate
  4. concentrationThe recovered organic layer was concentrated under reduced pressure
  5. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-c1b4b1885cbc441a8ce03ccc5ebb84de
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08058412B2

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