Tert-Butyl hypochlorite → HCID 86714599, compound

HRID 1025940Notes

Reaction equation

HRID 1025940 reaction equation
[CH3:1][C:2]1([CH2:8][C:9]([F:12])([F:11])[F:10])[CH2:6][O:5][C:4](=[O:7])[NH:3]1.C(O[Cl:18])(C)(C)C>CO>[Cl:18][N:3]1[C:2]([CH3:1])([CH2:8][C:9]([F:12])([F:10])[F:11])[CH2:6][O:5][C:4]1=[O:7]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 86714598HCID 86714598, compound

Product 1

HCID 86714599HCID 86714599, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-methyl-4-(2,2,2-trifluoroethyl)oxazolidin-2-one (400 mg, 2.18 mmol) in MeOH (6 ml) was cooled to 0° C. and tert-butylhypochlorite (294 mg, 2.73 mmol) was added. The solution was stirred for 2 h, concentrated in vacuo, and the residue purified by flash chromatography (0% to 10% MeOH in DCM) to afford the title compound as a white solid (350 mg, 74%). 1H NMR (CDCl3, 400 MHz) δ 1.54 (s, 3H), 2.48-2.57 (m, 1H), 2.64-2.76 (m, 1H), 4.28 (d, J=8.4 Hz, 1H), 4.45 (d, J=8.8 Hz, 1H). 19F NMR (CDCl3, 376 MHz) δ −60.93 (t, J=10.5 Hz). 13C NMR (CDCl3, 100 MHz) δ 20.8, 39.8 (q, J=28 Hz), 62.1, 72.8, 125 (q, J=265 Hz), 155.4. LRMS (ESI/APCI): 259 [M+H+CH3CN]+, 218 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by flash chromatography (0% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-4798f84c0652495d8e85845b5271d6ca
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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