m-Chloroperbenzoic acid → HCID 23114277, compound

HRID 2376512Notes

Reaction equation

HRID 2376512 reaction equation
[CH2:1]([C:3]1[C:11]2[S:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[C:7]=2[C:6]([CH3:21])=[C:5]([NH:22][C:23](=[O:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:4]=1[CH3:30])[CH3:2].C(=O)([O-])[OH:32].[Na+].ClC1C=CC=C(C(OO)=O)C=1.S([O-])(O)(=O)=O.[Na+]>ClCCl>[CH2:1]([C:3]1[C:11]2[S:10](=[O:32])[CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([CH3:19])[CH3:20])=[CH:14][CH:13]=3)[C:7]=2[C:6]([CH3:21])=[C:5]([NH:22][C:23](=[O:29])[CH2:24][C:25]([CH3:27])([CH3:26])[CH3:28])[C:4]=1[CH3:30])[CH3:2]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 516919Sodium BisulfateHCID 23113999HCID 23113999, compound

Product 1

HCID 23114277HCID 23114277, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(7-ethyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide (225 mg, 0.512 mmol) obtained in Example 164 and sodium hydrogen carbonate (65 mg, 1.01 mmol) in dichloromethane (10 mL) was added m-chloroperbenzoic acid (124 mg, 0.716 mmol) at 0° C. and the resulting mixture was stirred at room temperature for two hours. To reaction solution was added an aqueous sodium hydrogensulfate solution, the organic layer separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 50 mg (yield: 22%) of the title compound. Melting point: 195-196° C. (ethyl acetate-hexane).

Workup

  1. customTo reaction solution
  2. customthe organic layer separated
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. washThe combined organic layers were washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-dec423f989a440feb6284bed7e8023c3
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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