Tert-Butyl hypochlorite → N-((3-Chloro-4-methyl-2-oxooxazolidin-4-yl)methyl)-N,N-dimethylpropan-1-aminium chloride

HRID 1023487Notes

Reaction equation

HRID 1023487 reaction equation
[Cl-:1].[CH3:2][N+:3]([CH3:15])([CH2:7][C:8]1([CH3:14])[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[CH2:4][CH2:5][CH3:6].C(O[Cl:21])(C)(C)C>CO>[Cl-:21].[Cl:1][N:9]1[C:8]([CH2:7][N+:3]([CH3:2])([CH3:15])[CH2:4][CH2:5][CH3:6])([CH3:14])[CH2:12][O:11][C:10]1=[O:13]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 68562483N,N-Dimethyl-N-((4-methyl-2-oxooxazolidin-4-yl)methyl)propan-1-aminium chloride

Product 1

HCID 53234010N-((3-Chloro-4-methyl-2-oxooxazolidin-4-yl)methyl)-N,N-dimethylpropan-1-aminium chlorideYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N,N-dimethyl-N-((4-methyl-2-oxooxazolidin-4-yl)methyl)propan-1-aminium chloride (6.51 mmol) in MeOH (5 ml) was added, dropwise, tert-butylhypochlorite (˜2.5 ml) until the reaction mixture was clear with white precipitate. The solution was filtered through a 0.45 μm nylon filter, then evaporated and purified on preparative HPLC (H2O/MeOH) to afford the title compound as a white foam (248.1 mg, 0.9648 mmol, 15% over two steps). 1H NMR (D2O, 400 MHz) δ 0.99 (t, J=7.2 Hz, 3H), 1.64 (s, 3H), 1.8-2.0 (m, 2H), 3.24 (s, 3H), 3.26 (s, 3H), 3.40-3.45 (m, 2H), 3.75 (d, J=15.2 Hz, 1H), 3.82 (d, J=15.2 Hz, 1H), 4.62 (d, J=9.6 Hz, 1H), 4.90 (d, J=9.6 Hz, 1H). ESI/APCI expected for C10H20ClN2O2+: 235.12. Found: 235.

Workup

  1. filtrationThe solution was filtered through a 0.45 μm nylon
  2. filtrationfilter
  3. customevaporated
  4. custompurified on preparative HPLC (H2O/MeOH)

Sources & evidence

ORD record
ord-69425cec7d984db38e0be1b8b48dbbb6
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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