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

HRID 1698436노트

반응식

HRID 1698436 반응식
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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7d016a34850b4191b783e4a27b108e01
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163943B2

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