m-Chloroperbenzoic acid → HCID 86669143, compound

HRID 1422659Notes

Reaction equation

HRID 1422659 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:22]2[CH2:27][CH2:26][C:25]([CH2:34][C:35]([CH3:37])=[CH2:36])([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:24][C:23]2=[O:38])([CH3:21])[CH3:20])=[CH:15][CH:14]=1>C(Cl)Cl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:22]2[CH2:27][CH2:26][C:25]([CH2:34][C:35]3([CH3:37])[CH2:36][O:9]3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[O:24][C:23]2=[O:38])([CH3:21])[CH3:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66870053HCID 66870053, compound

Product 1

HCID 86669143HCID 86669143, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of m-CPBA (49.2 mg, 285 μmol) in CH2Cl2 (10 mL) was added 3-(2-(4-bromophenyl)propan-2-yl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (61 mg, 142.5 μmol). The reaction mixture was stirred at rt for 1 h. The solution was washed with 30 wt % aqueous sodium thiosulfate (50 mL×3), saturated aqueous sodium bicarbonate and brine successively. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 3-(2-(4-bromophenyl)propan-2-yl)-6-((2-methyloxiran-2-yl)methyl)-6-phenyl-1,3-oxazinan-2-one (57 mg, 90%).

Workup

  1. washThe solution was washed with 30 wt % aqueous sodium thiosulfate (50 mL×3), saturated aqueous sodium bicarbonate and brine successively
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4958e5b502a14cabbf2db565c175e517
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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