Water → Tert-butyl {5-[2-(benzyloxy)ethoxy]pyrazin-2-yl}carbamate

HRID 2192912ノート

反応式

HRID 2192912 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[N:13]=[CH:14][C:15](C(O)=O)=[N:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:23]([CH2:26]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.O.[C:46]([OH:50])([CH3:49])([CH3:48])[CH3:47]>>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[N:13]=[CH:14][C:15]([NH:23][C:26](=[O:35])[O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[N:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 5

HCID 962WaterHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 595710675-(2-Benzyloxyethoxy)pyrazine-2-carboxylic acid

生成物 1

HCID 59570995Tert-butyl {5-[2-(benzyloxy)ethoxy]pyrazin-2-yl}carbamate

実験手順

5-[2-(Benzyloxy)ethoxy]pyrazine-2-carboxylic acid (1.089 g) was suspended in tert-butyl alcohol (20 mL), and triethylamine (0.66 mL) and diphenylphosphoryl azide (0.9 mL) were added thereto. The reaction mixture was heated under reflux overnight and left to be cooled to room temperature. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine, and then dried over anhydrous magnesium sulfate. It was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-3:1) to obtain tert-butyl {5-[2-(benzyloxy)ethoxy]pyrazin-2-yl}carbamate (1.352 g) as a white solid.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. waitleft
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationIt was concentrated under reduced pressure
  8. customthe obtained crude product
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=5:1-3:1)

出典と根拠

ORDレコード
ord-c220927ab80846d9856ac095201107d3
出典データセット
uspto-grants-2012_12
特許番号
US08329707B2

反応ノート

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