Methanesulfonyl chloride → HCID 57947555, Verbindung

To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) followed by DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min and diluted with DCM (300 mL). The organic mixture washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was then dissolved in DMF (20.0 mL). To the resulting solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated at 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT and added water (20 mL) and EtOAc (200 mL). The organic layer was separated, washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps).

1. washThe organic mixture washed with NaHCO3, brine
2. dry with materialdried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was then dissolved in DMF (20.0 mL)
6. temperaturethe mixture was heated at 80° C. for 6 h
7. customthe completion of the reaction
8. temperatureThe mixture was cooled to RT
9. customThe organic layer was separated
10. washwashed with NaHCO3 and brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customThe residue was purified on silica gel column
15. additiona mixture of EtOAc and hexanes

ORD-Eintrag

ord-896f09e9f67b4e9a81d756ef5b320de5

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08895582B2