m-Chloroperbenzoic acid → HCID 66792841, compound

HRID 534987Notes

Reaction equation

HRID 534987 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:27])[C:18]([NH:20][CH:21]2[CH2:26][CH2:25]S[CH2:23][CH2:22]2)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=O)C=1.[OH:39][S:40]([O-:42])=O.[Na+].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:27])[C:18]([NH:20][CH:21]2[CH2:22][CH2:23][S:40](=[O:42])(=[O:39])[CH2:25][CH2:26]2)=[O:19])[CH2:15][CH2:16]1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 66792717HCID 66792717, compound

Product 1

HCID 66792841HCID 66792841, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxo-N-(tetrahydro-2H-thiopyran-4-yl)acetamide (Example 193, 0.21 g, 0.54 mmol) and m-chloroperbenzoic acid (0.29 g, 1.13 mmol) in ethyl acetate (10 mL) was stirred at 0° C. for 2 h. Then the mixture was added saturated NaHSO3 solution and stirred for 1 h. The mixture was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 60:40 to 0:100 then ethyl acetate/methanol 100/0 to 70/30) to give the title compound (0.20 g, 88%) as a white solid.

Workup

  1. stirringstirred for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 60:40 to 0:100

Sources & evidence

ORD record
ord-2e52bfd2bbe74502a87326152c80e174
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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