m-Chloroperbenzoic acid → HCID 12012915, compound

HRID 2361720Notes

Reaction equation

HRID 2361720 reaction equation
[C:1]([O-:4])(O)=[O:2].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1.O=[C:18]1[CH:25]2[CH2:26][C:21]3([NH:28][C:29](=[O:31])[CH3:30])[CH2:22][CH:23]([CH2:27][CH:19]1[CH2:20]3)C2.S(=O)(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:2]=[C:1]1[CH:23]2[CH2:22][C:21]3([NH:28][C:29](=[O:31])[CH3:30])[CH2:20][CH:19]([CH2:18][CH:25]([CH2:26]3)[O:4]1)[CH2:27]2

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 516919Sodium BisulfateHCID 5338964N-(4-oxo-1-adamantyl)acetamide

Product 1

HCID 12012915HCID 12012915, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid NaHCO3 (1.2 mol) and mCPBA (1 2 mmol, 77% purity) were added to a solution of ketone 1A (0.6 mmol) in DCM (5 mL) at 0° C. The reaction mixture was allowed to warm to rt and was maintained for 1 h. The reaction mixture was diluted with a saturated, aqueous solution of sodium bisulfate (10 mL) and was extracted with DCM (3×10 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (10/90 to 30/70 EtOAc/hexane) to provide lactone 16A in 90% yield. Data: LC/MS (ESR) m/z 224 [M+1]+.

Workup

  1. temperaturewas maintained for 1 h
  2. extractionwas extracted with DCM (3×10 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (10/90 to 30/70 EtOAc/hexane)

Sources & evidence

ORD record
ord-d0ae7dbef72740d1ba2376aa35b2b911
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

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