Methanol → (2S,3S)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-azido-2-hydroxyheptanamide

HRID 2053480ノート

反応式

HRID 2053480 の反応式
CO.[CH3:3][O:4][C:5](=[O:24])[C@@H:6]([NH:14][C:15]([C@@H:17]1[C@@H:19]([CH2:20][CH2:21][CH2:22][CH3:23])[O:18]1)=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N-:25]=[N+:26]=[N-:27].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>>[CH3:3][O:4][C:5](=[O:24])[C@@H:6]([NH:14][C:15](=[O:16])[C@@H:17]([OH:18])[C@@H:19]([N:25]=[N+:26]=[N-:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 4

HCID 887MethanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 33557Sodium AzideHCID 86618965(2S-trans)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-butyloxiranecarboxamide

生成物 1

HCID 59655559(2S,3S)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-azido-2-hydroxyheptanamide収率 69%

実験手順

A suspension of 30 ml of methanol containing 558 mg (1.84 mmol) of (2S-trans)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-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, under reduced pressure, the reaction mixture was concentrated and ethyl acetate was added to the concentrate, and then, 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 442 mg (Yield: 69%) of the title compound.

後処理

  1. temperaturewas refluxed for 5 hours
  2. customwas returned to room temperature, under reduced pressure
  3. concentrationthe reaction mixture was concentrated
  4. additionethyl acetate was 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-fa0a221f14554c708e46bd9a6093c271
出典データセット
uspto-grants-2008_02
特許番号
US07326799B2

反応ノート

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