Tert-Butyl hypochlorite → HCID 46202672, compound

HRID 1023485Notes

Reaction equation

HRID 1023485 reaction equation
[CH3:1][C:2]1([CH2:8][S:9]([CH2:12][CH2:13][S:14]([OH:17])(=[O:16])=[O:15])(=[O:11])=[O:10])[CH2:6][O:5][C:4](=[O:7])[NH:3]1.C(O[Cl:23])(C)(C)C>CO>[Cl:23][N:3]1[C:2]([CH2:8][S:9]([CH2:12][CH2:13][S:14]([OH:17])(=[O:16])=[O:15])(=[O:10])=[O:11])([CH3:1])[CH2:6][O:5][C:4]1=[O:7]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 59355180HCID 59355180, compound

Product 1

HCID 46202672HCID 46202672, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-((4-methyl-2-oxooxazolidin-4-yl)methylsulfonyl)ethanesulfonic acid (950 mg, 3.31 mmol) in MeOH (5 ml) was added, dropwise, tert-butylhypochlorite (500 ul, 4.2 mmol). The solution was stirred for 1 h, concentrated in vacuo, and purified by preparatory HPLC (H2O/MeOH) to afford the title compound as a clear oil (430.0 mg, 1.336 mmol, 40%). 1H NMR (D2O, 400 MHz) δ 1.60 (s, 3H), 3.3-3.4 (m, 2H), 3.6-3.7 (m, 2H), 3.80 (d, J=14.8 Hz, 1H), 3.96 (d, J=14.8 Hz, 1H), 4.47 (d, J=9.4 Hz, 1H), 5.05 (d, J=9.4 Hz, 1H). ESI/APCI expected for C7H12ClNO7S2: 320.97. Found: 320 (M−H+).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by preparatory HPLC (H2O/MeOH)

Sources & evidence

ORD record
ord-1111ebaaa8a64d4c9d13776e52ece1fd
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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