m-Chloroperbenzoic acid → HCID 11999235, compound

HRID 2102762Notes

Reaction equation

HRID 2102762 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([C:18]3([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=4)[C:26]4[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=4)[NH:20][C:19]3=[O:28])[CH2:13]2)=[O:11])=[CH:5][CH:4]=1.ClC1C=C(C(OO)=[O:45])C=CC=1>ClCCl>[CH3:1][S:2]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([C:18]3([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=4)[C:26]4[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=4)[NH:20][C:19]3=[O:28])[CH2:13]2)=[O:11])=[CH:5][CH:4]=1)=[O:45]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11999234HCID 11999234, compound

Product 1

HCID 11999235HCID 11999235, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the suspension of rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid (4-methylsulfanyl-phenyl)-amide (0.28 g, 0.52 mmol) (from Example 80 supra) in dichloromethane (5 mL) was added the suspension of 3-chloro-benzenecarboperoxoic acid (133 mg, 0.78 mmol) (Aldrich) in dichloromethane (2 mL). The mixture was stirred at room temperature for 30 minutes. The mixture was partitioned between dichlormethane and water. The aqueous layer was extracted with dichlormethane. The combined organic layer was washed with 10% of sodium sulfite solution, saturated sodium bicarbonate, brine, dried over MgSO4 and concentrated. The residue was purified by chromatography to give rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid (4-methanesulfinyl-phenyl)-amide as a grey solid (Yield 0.16 g, 57%).

Workup

  1. additionwas added
  2. customThe mixture was partitioned between dichlormethane and water
  3. extractionThe aqueous layer was extracted with dichlormethane
  4. washThe combined organic layer was washed with 10% of sodium sulfite solution, saturated sodium bicarbonate, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-82cada60fdc347e1a7a7a7f764bb8479
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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