Tert-Butyl hypochlorite → HCID 46206227, compound

HRID 1023479Notes

Reaction equation

HRID 1023479 reaction equation
[Cl-:1].[CH3:2][N+:3]([CH3:13])([CH3:12])[CH2:4][C:5]1([CH3:11])[CH2:9][O:8][C:7](=[O:10])[NH:6]1.C(O[Cl:19])(C)(C)C>CO>[Cl-:19].[Cl:1][N:6]1[C:5]([CH2:4][N+:3]([CH3:13])([CH3:12])[CH3:2])([CH3:11])[CH2:9][O:8][C:7]1=[O:10]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 68561944HCID 68561944, compound

Product 1

HCID 46206227HCID 46206227, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N,N,N-trimethyl-1-(4-methyl-2-oxooxazolidin-4-yl)methanaminium chloride (1.52 mmol) in MeOH (1 ml) was added, dropwise, tert-butylhypochlorite (250 uL, 2.10 mmol). The solution was stirred for 3 h, evaporated, and purified by preparatory HPLC (H2O/CH3CN) to afford the title compound as a yellow foam (115.6 mg, 0.475 mmol, 31% over two steps). 1H NMR (D2O, 400 MHz) δ 1.64 (s, 3H), 3.31 (s, 9H), 3.80 (d, J=15.2 Hz, 1H), 3.88 (d, J=14.8 Hz, 1H), 4.61 (d, J=9.6 Hz, 1H), 4.93 (d, J=10.0 Hz, 1H). ESI/APCI expected for C8H16ClN2O2+: 207.09. Found: 207 (M+).

Workup

  1. customevaporated
  2. custompurified by preparatory HPLC (H2O/CH3CN)

Sources & evidence

ORD record
ord-626f6d837e92438486f6aad6838edcf4
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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