m-Chloroperbenzoic acid → N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide

HRID 1487063Notes

Reaction equation

HRID 1487063 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:18]=[C:17]([F:19])[C:16]([CH:20]=[CH2:21])=[C:15]([F:22])[CH:14]=1)(=[O:12])=[O:11].ClC1C=C(C=CC=1)C(OO)=[O:32]>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:18]=[C:17]([F:19])[C:16]([CH:20]2[CH2:21][O:32]2)=[C:15]([F:22])[CH:14]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 89875754N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutyl-4-vinylbenzenesulfonamide

Product 1

HCID 89875867N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2,4-dimethylphenyl)-3,5-difluoro-N-isobutyl-4-vinylbenzenesulfonamide (1.5 g, 3.95 mmol) in dichloromethane (DCM) at 0° C. was added meta-chloroperoxybenzoic acid (mCPBA) (2.73 g, 15.81 mmol) and the reaction mixture stirred for 24 hours from 0° C. to 25° C. Additional mCPBA (1.364 g, 7.91 mmol) was then added and the reaction stirred for a further 6 hours. The reaction was then washed with water (2 mL), sodium hydroxide solution (2M, 2 mL) and brine (2 mL), then evaporated in vacuo. The crude was purified by flash silica (Si) chromatography (0-100% dichloromethane-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the required product, 926 mg, as a yellow oil. LCMS [LCMS2] Rt. 1.45, m/z (ES+) 396 (M+H).

Workup

  1. stirringthe reaction stirred for a further 6 hours
  2. washThe reaction was then washed with water (2 mL), sodium hydroxide solution (2M, 2 mL) and brine (2 mL)
  3. customevaporated in vacuo
  4. customThe crude was purified by flash silica (Si) chromatography (0-100% dichloromethane-cyclohexane gradient)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-894ff6d8b25940ffba7ff8816f07f7e3
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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