Triethylamine → HCID 131731731, compound

A solution of benzyl[(2R,3S)-3-fluoro-1-hydroxypentan-2-yl]carbamate (2.4 g) in chloroform (40 mL) was cooled in ice, triethylamine (2 mL) and methanesulfonyl chloride (0.8 mL) were added thereto, and the mixture was stirred for 30 min. Saturated sodium hydrogen carbonate was added thereto, followed by extraction with chloroform and drying over anhydrous magnesium sulfate. After the desiccant was filterred off, the solvent was distilled off under reduced pressure, and the residue was dissolved in DMF (40 mL). Sodium azide (3.06 g) was added thereto, and the mixture was stirred at 60° C. for 2 hr. Water was added thereto, the resulting mixture was extracted with ethyl acetate, and the organic layer was washed with water and brine. After drying over anhydrous magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was dissolved in THF (50 mL), triphenylphosphine (3.59 g) and water (10 mL) were added thereto, and the resulting mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=98:2-80:20) to afford benzyl[(2R,3S)-1-amino-3-fluoropentan-2-yl]carbamate (2.34 g).

1. extractionfollowed by extraction with chloroform
2. dry with materialdrying over anhydrous magnesium sulfate
3. distillationthe solvent was distilled off under reduced pressure
4. dissolutionthe residue was dissolved in DMF (40 mL)
5. additionSodium azide (3.06 g) was added
6. stirringthe mixture was stirred at 60° C. for 2 hr
7. additionWater was added
8. extractionthe resulting mixture was extracted with ethyl acetate
9. washthe organic layer was washed with water and brine
10. dry with materialAfter drying over anhydrous magnesium sulfate
11. filtrationthe desiccant was filtered off
12. distillationthe solvent was distilled off under reduced pressure
13. dissolutionThe residue was dissolved in THF (50 mL)
14. additiontriphenylphosphine (3.59 g) and water (10 mL) were added
15. stirringthe resulting mixture was stirred at room temperature overnight
16. distillationThe solvent was distilled off under reduced pressure
17. customthe residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=98:2-80:20)

ORD record

ord-832037ca36f94a11a636f679504db461

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796272B2