Methanesulfonyl chloride → HCID 57947555, compound

HRID 409854Notes

Reaction equation

HRID 409854 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.CCN(C(C)C)C(C)C.[N-:35]=[N+:36]=[N-:37].[Na+]>C(Cl)Cl.CCOC(C)=O.O>[N:35]([CH2:11][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N+:36]=[N-:37]

Participants

8

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 81531DiisopropylethylamineHCID 14427183tert-Butyl [(2S)-1-(benzyloxy)-3-hydroxypropan-2-yl]carbamate

Product 1

HCID 57947555HCID 57947555, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d25a15b8126441798e801e0215bfe87b
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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