m-Chloroperbenzoic acid → HCID 71714787, compound

HRID 70470Notes

Reaction equation

HRID 70470 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:10]([NH:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[S:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])(=[O:12])=[O:11].C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)Cl.CCOC(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:10]([NH:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[S:21]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:36])(=[O:11])=[O:12]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 71714789HCID 71714789, compound

Product 1

HCID 71714787HCID 71714787, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)propanoate (181 mg, 0.43 mmol) in CH2Cl2 (4 ml) was added mCPBA (153 mg, ˜0.64 mmol). The reaction was stirred at room temperature for 1 hour, diluted with EtOAc, extracted with saturated aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (25-100% EtOAc in hexane, then 10% MeOH in CH2Cl2) to yield the title compound (87 mg, 46%).

Workup

  1. extractionextracted with saturated aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (25-100% EtOAc in hexane

Sources & evidence

ORD record
ord-32aaf36af0cd4ba3969d33794559561b
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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