Methanesulfonyl chloride → HCID 57947555, compound

HRID 409775Notes

Reaction equation

HRID 409775 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.CN(C=O)C>[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

9

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 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 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) and DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min. The mixture was diluted with DCM (300 mL), washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in DMF (20 mL). To this DMF solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated to 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT, water (20 mL) and EtOAc (200 mL) were added. The organic layer was separated, washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The rude was purified on silica gel column to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps).

Workup

  1. washwashed with NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe crude product was dissolved in DMF (20 mL)
  6. temperaturethe mixture was heated to 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, brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe rude was purified on silica gel column

Sources & evidence

ORD record
ord-8a8d035149714f0eacd504040287c473
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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