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

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.

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

ORD record

ord-a018b0d294c848129f4ad1acaf93682a

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07326799B2