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

HRID 2368394ノート

反応式

HRID 2368394 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6a6b1baad731490cbfd9df1e2e91bfe3
出典データセット
uspto-grants-2014_04
特許番号
US08703768B2

反応ノート

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