Potassium Carbonate → (2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

(2S,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane (0.40 g) and potassium carbonate (0.37 g) were added to methanol (8 ml), and the mixture was stirred at room temperature for 6 hours. The inorganic salt was filtered off from the reaction solution, and the filtrate was then concentrated under reduced pressure. To the residue was added water, and the solution was extracted with methylene chloride. The resulting methylene chloride layer was washed with a 20% citric acid aqueous solution, and the solvent was then distilled off under reduced pressure. Ethyl acetate (2 ml) was added to the residue. The mixture was heat-dissolved, and crystallized by being cooled to room temperature. Further, n-hexane (4 ml) was added thereto, and the resulting mixture was stirred while being cooled with ice. Crystals were separated, and dried to obtain the crystals (0.30 g) of desired (2S,3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane in a yield of 85%.

1. filtrationThe inorganic salt was filtered off from the reaction solution
2. concentrationthe filtrate was then concentrated under reduced pressure
3. additionTo the residue was added water
4. extractionthe solution was extracted with methylene chloride
5. washThe resulting methylene chloride layer was washed with a 20% citric acid aqueous solution
6. distillationthe solvent was then distilled off under reduced pressure
7. additionEthyl acetate (2 ml) was added to the residue
8. dissolutionThe mixture was heat-dissolved
9. customcrystallized
10. temperatureby being cooled to room temperature
11. additionFurther, n-hexane (4 ml) was added
12. stirringthe resulting mixture was stirred
13. temperaturewhile being cooled with ice
14. customCrystals were separated
15. customdried

ORD record

ord-9474b6bbaf714a2abac77d943e120789

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06500985B2