Potassium Carbonate → 2-(4-Methyl-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-propionic acid

HRID 732064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732064
Cl[C@H:2]([CH3:6])[C:3]([OH:5])=[O:4].[CH3:7][N:8]1[C:12]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[N:11][N:10]=[C:9]1[SH:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C=O)C>[CH3:7][N:8]1[C:12]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[N:11][N:10]=[C:9]1[S:18][CH:2]([CH3:6])[C:3]([OH:5])=[O:4]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27245402-Chloropropionic acid, (+)-HCID 178481692HCID 178481692, Verbindung

Produkt 1

HCID 177434532-(4-Methyl-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-propionic acidAusbeute 12,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(R)-2-chloro-propionic acid (500 mg, 4.6 mmol), 4-methyl-5-thiophen-2-yl-4H-[1,2,4]triazole-3-thiol (1.09 g, 5.58 mmol) and potassium carbonate (1.94 g, 14.03 mmol) were dissolved in acetonitrile (15 ml) at room temperature. Reaction proceeded for 2.5 h and was partitioned between ethyl acetate (350 ml) and water 3 times, washed with 1 M HCl, once with saturated brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. Reaction was not completed at this stage and the crude was stirred in DMF (10 ml) overnight. Extraction was repeated and purification was performed by SPE (solid phase extraction) chromatography on silica gel using 300 ml ethyl acetate, 100 ml 1%, and 100 ml 3% formic acid in ethyl acetate, yielding title compound (150.7 mg, 12%) 1H-NMR (CDCl3), d (ppm): 7.52 (dd, 2H), 7.19 (m, 1H), 4.21 (q, 1H), 3.78 (s, 3H), 1.64 (d, 3H).

Aufarbeitung

  1. customReaction
  2. customwas partitioned between ethyl acetate (350 ml) and water 3 times
  3. washwashed with 1 M HCl, once with saturated brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customReaction
  8. extractionExtraction
  9. custompurification
  10. extractionwas performed by SPE (solid phase extraction) chromatography on silica gel using 300 ml ethyl acetate, 100 ml 1%, and 100 ml 3% formic acid in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-dae6f7238f11435fabb395d74f55e783
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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