N-[(3S)-2,6-dioxooxan-3-yl]-2,2,2-trifluoroacetamide → alpha-L-glutamyl-5-aminopyridine-2-carbonitrile

HRID 327327

Reaktionsgleichung

Reaktionsgleichung von HRID 327327
FC(F)(F)C([NH:5][C@@H:6]1[C:12](=[O:13])[O:11][C:9](=[O:10])[CH2:8][CH2:7]1)=O.[C:16]([C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][N:19]=1)#[N:17]>O1CCCC1>[NH2:5][C@H:6]([C:12]([C:23]1[C:18]([C:16]#[N:17])=[N:19][CH:20]=[C:21]([NH2:24])[CH:22]=1)=[O:13])[CH2:7][CH2:8][C:9](=[O:10])[OH:11]

Komponenten

4

Edukt 2

HCID 2779007N-[(3S)-2,6-dioxooxan-3-yl]-2,2,2-trifluoroacetamideHCID 38713955-Aminopyridine-2-carbonitrile

Produkt 1

HCID 18650754alpha-L-glutamyl-5-aminopyridine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Alpha-L-glutamyl-5-aminopyridine-2-carbonitrile is prepared by the method described in J. Med. Chem., 1973, 16, 163-166. A solution of 5.5 g (24.4 mmol) of N-trifluoroacetyl-L-glutamic anhydride and 2.6 g (21.8 mmol) of 2-cyano-5-aminopyridine (prepared according to tetrahydrofuran (20 cm3) is stirred for 12 h at 40° C. The solvent is then removed and the residue is dissolved in a 1% solution of sodium carbonate (80 cm3). The solution is rapidly washed with methylene chloride (3×30 cm3) and then acidified to pH 2-3 with a 6 N solution of HCl. Extraction with a solution of ethyl acetate (3×50 cm3), followed by drying over sodium sulfate and then evaporation of the solvent, gives 5.1 g of a crude product, N-trifluoroacetyl-alpha-L-glutamyl-5-aminopyridine-2-carbonitrile, which is obtained pure (melting point: 157° C.) after recrystallization several times from an ethanol/hexane mixture (40/60). After treatment of this compound with a 7.5% solution of ammonia for 4 h at 20° C., followed by concentration to dryness, alpha-L-glutamyl-5-aminopyridine-2-carbonitrile is finally obtained (quantitative yield, melting point: 152° C.).

Aufarbeitung

  1. customThe solvent is then removed
  2. dissolutionthe residue is dissolved in a 1% solution of sodium carbonate (80 cm3)
  3. washThe solution is rapidly washed with methylene chloride (3×30 cm3)
  4. extractionExtraction with a solution of ethyl acetate (3×50 cm3)
  5. dry with materialby drying over sodium sulfate
  6. customevaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-b9da0b736dc24ec7884417a54f499f5e
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05272272

Verknüpfte Notizen

Wird geladen…