m-Chloroperbenzoic acid → HCID 89876041, compound

HRID 1487071Notes

Reaction equation

HRID 1487071 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:22][CH:23]([CH3:25])[CH3:24])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH2:20])=[C:15]([OH:21])[CH:14]=1)(=[O:12])=[O:11].ClC1C=C(C=CC=1)C(OO)=[O:31]>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:22][CH:23]([CH3:25])[CH3:24])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:20][O:31]2)=[C:15]([OH:21])[CH:14]=1)(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 89876014HCID 89876014, compound

Product 1

HCID 89876041HCID 89876041, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of N-(2,4-dimethylphenyl)-3-hydroxy-N-isobutyl-4-vinylbenzenesulfonamide (100.8 mg, 0.280 mmol) in dichloromethane (DCM) (20 mL) stirred under nitrogen at 0° C. was added meta-chloroperoxybenzoic acid (mCPBA) (194 mg, 1.122 mmol) portionwise. The reaction mixture was stirred at 0° C. for 30 minutes, then for 72 hours at room temperature. DCM (20 mL) was added to the mixture and the organic phase washed with water (20 mL), dried using a hydrophobic frit and concentrated under a stream of nitrogen to give the crude product, 60 mg, which was used directly in the next step with no further purification. LCMS [LCMS2] Rt 1.42 min, m/z (ES−) 374 (M−H).

Workup

  1. waitfor 72 hours at room temperature
  2. washthe organic phase washed with water (20 mL)
  3. customdried
  4. concentrationconcentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-47fb7e64fd5e40e4b4df56517a0330b9
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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