m-Chloroperbenzoic acid → HCID 86696139, compound

HRID 1426004Notes

Reaction equation

HRID 1426004 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([N:21]2[CH2:26][CH2:25][C:24]([CH2:31][CH:32]3[CH2:34][CH2:33]3)([CH2:27][C:28]([CH3:30])=[CH2:29])[O:23][C:22]2=[O:35])[CH3:20])=[CH:15][CH:14]=1>C(Cl)Cl>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([N:21]2[CH2:26][CH2:25][C:24]([CH2:31][CH:32]3[CH2:34][CH2:33]3)([CH2:27][C:28]3([CH3:30])[CH2:29][O:9]3)[O:23][C:22]2=[O:35])[CH3:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66735700HCID 66735700, compound

Product 1

HCID 86696139HCID 86696139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (455 mg) was added to a solution of 3-[(S)-1-(4-bromophenyl)-ethyl]-6-(cyclopropylmethyl)-6-(2-methylallyl)-1,3-oxazinan-2-one (516 mg) in CH2Cl2 (15 mL) at 0° C. The mixture was stirred at room temperature overnight. The mixture was then washed with 3% aqueous Na2S2O3 solution and saturated aqueous NaHCO3 solution. The aqueous washing phase was extracted with ethyl acetate (3×30 mL) and the combined organic layer was washed with brine, dried (Na2SO4), and concentrated to afford the crude title compound which was used without further purification. Yield: 490 mg (91% of theory).

Workup

  1. washThe mixture was then washed with 3% aqueous Na2S2O3 solution and saturated aqueous NaHCO3 solution
  2. extractionThe aqueous washing phase was extracted with ethyl acetate (3×30 mL)
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-368f1675a7e1459ab3e5b13c78223d12
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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