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

HRID 1023481Notes

Reaction equation

HRID 1023481 reaction equation
[Cl-:1].[CH3:2][N+:3]([CH3:14])([CH2:6][C:7]1([CH3:13])[CH2:11][O:10][C:9](=[O:12])[NH:8]1)[CH2:4][CH3:5].C(O[Cl:20])(C)(C)C>CO>[Cl-:20].[Cl:1][N:8]1[C:7]([CH2:6][N+:3]([CH3:2])([CH3:14])[CH2:4][CH3:5])([CH3:13])[CH2:11][O:10][C:9]1=[O:12]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 68563428N,N-Dimethyl-N-((4-methyl-2-oxooxazolidin-4-yl)methyl)ethanaminium chloride

Product 1

HCID 46186812N-((3-Chloro-4-methyl-2-oxooxazolidin-4-yl)methyl)-N,N-dimethylethanaminium chlorideYield 38.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N,N-dimethyl-N-((4-methyl-2-oxooxazolidin-4-yl)methyl)ethanaminium chloride (6.76 mmol) in MeOH (10 ml) was added, dropwise, tert-butylhypochlorite (1.6 ml, 10 mmol). The solution was stirred for 2 h, evaporated, and purified by preparative HPLC (H2O/MeOH) to afford the title compound as a white foam (667 mg, 2.59 mmol, 38% over two steps). 1H NMR (D2O, 400 MHz) δ 1.44 (t, J=7.2 Hz, 3H), 1.65 (s, 3H), 3.22 (s, 3H), 3.25 (s, 3H), 3.57 (q, J=7.2 Hz, 2H), 3.76-3.80 (m, 2H), 4.61 (d, J=9.6 Hz, 1H), 4.90 (d, J=9.6 Hz, 1H). ESI/APCI expected for C9H18ClN2O2+: 221.11. Found: 221.

Workup

  1. customevaporated
  2. custompurified by preparative HPLC (H2O/MeOH)

Sources & evidence

ORD record
ord-d3e0a050381f46788a54d7ba77cb936f
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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