Methanol → (2S,3S)-N-butyl-3-azido-2-hydroxyheptanamide

HRID 1698436ノート

反応式

HRID 1698436 の反応式
CO.[CH2:3]([NH:7][C:8]([C@@H:10]1[C@@H:12]([CH2:13][CH2:14][CH2:15][CH3:16])[O:11]1)=[O:9])[CH2:4][CH2:5][CH3:6].[N-:17]=[N+:18]=[N-:19].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>>[CH2:3]([NH:7][C:8](=[O:9])[C@@H:10]([OH:11])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:13][CH2:14][CH2:15][CH3:16])[CH2:4][CH2:5][CH3:6]

参加物

5

反応物 4

HCID 887MethanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 33557Sodium AzideHCID 86618964(2S-trans)-N-butyl-3-butyloxiranecarboxamide

生成物 1

HCID 59655565(2S,3S)-N-butyl-3-azido-2-hydroxyheptanamide収率 68%

実験手順

A suspension of 30 ml of methanol containing 366 mg (1.84 mmol) of (2S-trans)-N-butyl-3-butyloxiranecarboxamide, 239 mg (3.68 mmol) of sodium azide and 228 mg (1.89 mmol) of anhydrous magnesium sulfate was refluxed for 5 hours. After the temperature of the reaction mixture was returned to room temperature, the reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the concentrate, and the resulting mixture was washed successively with water, and then a saturated NaCl solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to obtain 304 mg (Yield: 68%) of the title compound.

後処理

  1. temperaturewas refluxed for 5 hours
  2. customwas returned to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure, ethyl acetate
  4. additionwas added to the concentrate
  5. washthe resulting mixture was washed successively with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-7d016a34850b4191b783e4a27b108e01
出典データセット
uspto-grants-2012_04
特許番号
US08163943B2

反応ノート

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