Dimethylformamide → Sutezolid

HRID 2294078Notes

Reaction equation

HRID 2294078 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH:17]([CH2:19]OS(C3C=CC(C)=CC=3)(=O)=O)[O:16][C:15]2=[O:31])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1.[N-]=[N+]=[N-].[Na+].[CH3:36][C:37]#[N:38].C(Cl)(Cl)Cl.CN(C=[O:47])C>CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:38][C:37](=[O:47])[CH3:36])[O:16][C:15]2=[O:31])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 22555007Acetonitrile chloroformHCID 85218459HCID 85218459, compound

Product 1

HCID 465951SutezolidYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

The [[3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-p-toluenesulfonate (2.0 g, 4.287 mmol) was dissolved in dry DMF (15 mL) and then treated with solid NaN3 (1.67 g, 25.722 mmol). The reaction was heated to 65° C. (external temperature) for 6 hours, after which the reaction was allowed to cool to ambient temperature, stirring over a long weekend (158 hours). At this point, the reaction was found to be complete by TLC (6% CH3CN/CHCl3, UV short wave). The reaction was diluted with EtOAc (300 mL) and then washed with water (3×250 mL). The aqueous portions were back-extracted with more EtOAc (2×150 mL). The EtOAc portions were combined, dried over Na2SO4, filtered and concentrated under reduced pressure to give 1.447 g (100%) of the title compound as an off-white solid with a melting point of 91.5°-93° C. and a HRMS (M+) calculated for C14 H16N5O5FS 337.1009, found 337.1009.

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed with water (3×250 mL)
  3. extractionThe aqueous portions were back-extracted with more EtOAc (2×150 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f213aa0865dc4da590d7fd1a0f1b06c2
Source dataset
uspto-grants-1997_11
Patent number
US05688792

Reaction notes

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