Methanol → (2S,3S)-N-[(2S)-1-methoxy-1-oxo-3-phenyl-2-propyl]-3-azido-2-hydroxyheptanamide
Reaction equation
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]=1Participants
Procedure
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.
Workup
- temperaturewas refluxed for 5 hours
- customwas returned to room temperature, under reduced pressure
- concentrationthe reaction mixture was concentrated
- additionethyl acetate was added to the concentrate
- washthe resulting mixture was washed successively with water
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was removed under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-dfabff5db9fe48d69b1c241f07cbd92b
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163943B2
Reaction notes
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