m-Chloroperbenzoic acid → HCID 11999236, compound

HRID 2102763Notes

Reaction equation

HRID 2102763 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=4)[C:27]4[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:29])[CH2:14]2)=[O:12])=[CH:6][CH:5]=1)=[O:3].ClC1C=C(C(OO)=[O:46])C=CC=1>ClCCl>[CH3:1][S:2]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=4)[C:27]4[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:29])[CH2:14]2)=[O:12])=[CH:8][CH:9]=1)(=[O:46])=[O:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11999235HCID 11999235, compound

Product 1

HCID 11999236HCID 11999236, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 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 (85 mg, 0.15 mmol) (from Example 81 supra) in dichloromethane (4 mL) was added 3-chloro-benzenecarboperoxoic acid (52.6 mg, 0.3 mmol) (Aldrich). The mixture was stirred at room temperature for 1 hour. The mixture was partitioned between dichlormethane and water. The aqueous layer was extracted with dichlormethane. The combined organic layer was washed with 2% 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-methanesulfonyl-phenyl)-amide as a pale yellow solid. (Yield 81 mg, 93%).

Workup

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

Sources & evidence

ORD record
ord-1faa5aff1d734e29800bd5fb40e2b61d
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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