Dimethyl Sulfoxide → 3-(Bis(tert-butoxycarbonyl)amino)-6-(2,2,2-trifluoro-ethoxy)-pyrazine-2-carboxylic acid methyl ester

HRID 2368394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368394
[C:1]([O:5][C:6]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12](Br)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:27][C:28]([F:32])([F:31])[CH2:29][OH:30].C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>C(OCC)(=O)C>[CH3:19][O:18][C:16]([C:10]1[C:9]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:14][CH:13]=[C:12]([O:30][CH2:29][C:28]([F:32])([F:31])[F:27])[N:11]=1)=[O:17]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 86660188Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate

Produkt 1

HCID 700980663-(Bis(tert-butoxycarbonyl)amino)-6-(2,2,2-trifluoro-ethoxy)-pyrazine-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate (500 mg, 1.16 mmol), 2,2,2-trifluoroethanol (84 μl, 1.16 mmol), cesium carbonate (415 mg, 1.27 mmol) and dry DMSO (5 ml) was stirred at r.t. for 3 h. The reaction mixture was poured into ethyl acetate (100 ml) and extracted with saturated sodium bicarbonate (aqueous solution). The organic layer was washed with water and brine and the aqueous layers were back-extracted with ethyl acetate. The combined organic layers were dried, evaporated and the product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as white solid (456 mg, 87%).

Aufarbeitung

  1. extractionextracted with saturated sodium bicarbonate (aqueous solution)
  2. washThe organic layer was washed with water and brine
  3. extractionthe aqueous layers were back-extracted with ethyl acetate
  4. customThe combined organic layers were dried
  5. customevaporated
  6. customthe product was obtained
  7. customafter purification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6a6b1baad731490cbfd9df1e2e91bfe3
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703768B2

Notizen zur Reaktion

Wird geladen…