m-Chloroperbenzoic acid → HCID 68968184, compound

HRID 2220217Notes

Reaction equation

HRID 2220217 reaction equation
[C:1]([N:4]1[CH2:11][C:10]2[CH:12]=[CH:13][C:14]([S:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:15][C:9]=2[CH:8]=[CH:7][C:6]2[CH:21]=[CH:22][CH:23]=[CH:24][C:5]1=2)(=[O:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C(Cl)Cl>[C:1]([N:4]1[CH2:11][C:10]2[CH:12]=[CH:13][C:14]([S:16]([CH2:17][CH2:18][CH2:19][CH3:20])=[O:33])=[CH:15][C:9]=2[CH:8]=[CH:7][C:6]2[CH:21]=[CH:22][CH:23]=[CH:24][C:5]1=2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68891326HCID 68891326, compound

Product 1

HCID 68968184HCID 68968184, compoundYield 135.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound Example 287A (32 mg, 0.095 mmol) in CH2Cl2 (5 mL) at 0° C. was added mCPBA (13 mg, 0.05 mmol). The solution was stirred for 1 hour at 0° C. and for 1 hour at room temperature. The reaction was quenched by adding NaHCO3 solution. The aqueous layer was extracted with EtOAc (3×2 mL). The combined EtOAc extracts were washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (SiO2, 2:1 hexane/EtOAc) to give the title compound (24 mg, 77 %). HPLC Rt=3.7 min. m/z=354(M+H+).

Workup

  1. customat 0° C.
  2. customThe reaction was quenched
  3. additionby adding NaHCO3 solution
  4. extractionThe aqueous layer was extracted with EtOAc (3×2 mL)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (SiO2, 2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-a29b8f833aa44325b7a5ac9d71fa6c14
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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