Sodium Azide → HCID 53868579, compound

HRID 617752Notes

Reaction equation

HRID 617752 reaction equation
[C@H:1]12[CH2:26][C@H:4]([N:5]([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@@H:16]([CH2:18]CS([O-])(=O)=O)[O:15][C:14]4=[O:24])=[CH:9][C:8]=3[F:25])[CH2:6]1)[CH2:3][O:2]2.[N-:27]=[N+:28]=[N-:29].[Na+].CO.C(Cl)(Cl)Cl>CCOC(C)=O>[C@H:1]12[CH2:26][C@H:4]([N:5]([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][N:27]=[N+:28]=[N-:29])[O:15][C:14]4=[O:24])=[CH:9][C:8]=3[F:25])[CH2:6]1)[CH2:3][O:2]2

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 21584188Chloroform methanolHCID 86754454HCID 86754454, compound

Product 1

HCID 53868579HCID 53868579, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of (R)-[[3-[4-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]methanesulfonate (0.869 g, 2.26 mmol) in dry DMP (10 mL) was treated with solid NaN3 (0.732 g, 11.3 mmol) at ambient temperature under N2. The mixture was then heated to 65° C. and reaction progress monitored by TLC. After 7.5 h at this temperature, TLC analysis (5% MeOH/CHCl3) revealed the reaction to complete. The reaction mixture was diluted with EtOAc (100 mL), washed with H2O (3×15 mL) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 0.692 g (92%) of the title compound as a tan solid. An analytical sample was prepared by recrystallization from 1:1 EtOc/hexane as an off-white solid with mp 101-102.5° C. and MS(EI) 333 (M+).

Workup

  1. customreaction progress
  2. customthe reaction
  3. washwashed with H2O (3×15 mL) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83e8587638cb46e1b1265d5974e52468
Source dataset
uspto-grants-1999_09
Patent number
US05952324

Reaction notes

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