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

HRID 1698440노트

반응식

HRID 1698440 반응식
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

참가 물질

5

반응물 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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dfabff5db9fe48d69b1c241f07cbd92b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163943B2

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