Sodium Azide → HCID 53639939, compound

HRID 1418652Notes

Reaction equation

HRID 1418652 reaction equation
[Si:1]([O:8][CH:9]1[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@@H:22]([CH2:24]CS([O-])(=O)=O)[O:21][C:20]3=[O:30])=[CH:15][C:14]=2[F:31])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N-:32]=[N+:33]=[N-:34].[Na+].CO.C(Cl)(Cl)Cl.[N-]=[N+]=[N-]>CN(C)C=O.C(OCC)(=O)C>[Si:1]([O:8][CH:9]1[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][N:32]=[N+:33]=[N-:34])[O:21][C:20]3=[O:30])=[CH:15][C:14]=2[F:31])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 21584188Chloroform methanolHCID 86753886HCID 86753886, compound

Product 1

HCID 53639939HCID 53639939, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Crude (R)-[[3-[4-[3-[(tert-butyldimethylsilyl)oxy]-1-azetidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]methanesulfonate (9.42 mmol) was dissolved in dry N,N-dimethylformamide (50 mL) and treated with sodium azide (4.42 g, 68.0 mmol) at ambient temperature. The reaction mixture was warmed to 65° C. under nitrogen for 4 h. TLC analysis (5% methanol/chloroform) at this time revealed the reaction to be complete. The reaction mire was diluted with ethyl acetate (100 mL) and washed with water (3×25 mL) and brine, dried over sodium sulfate, filtered and concentrated in vacuo to an amber solid. Chromatography over silica gel (125 g), eluting with a gradient of 10-20% ethyl acetate/hexane, afforded, after concentration of appropriate fractions, 2.21 g (56% for 3 steps) of the title azide as a white solid with mp 121°-122.5° C. and MS(EI) 421 (M+).

Workup

  1. customthe reaction
  2. washwashed with water (3×25 mL) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to an amber solid
  6. washChromatography over silica gel (125 g), eluting with a gradient of 10-20% ethyl acetate/hexane
  7. customafforded

Sources & evidence

ORD record
ord-8f506ded1a5d4a6c8971ff9552e936da
Source dataset
uspto-grants-1999_03
Patent number
US05883093

Reaction notes

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