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

HRID 467797Notes

Reaction equation

HRID 467797 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-64c2cdb3fc31479f9410e66a856b2ec9
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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