m-Chloroperbenzoic acid → HCID 71714787, compound

HRID 520978Notes

Reaction equation

HRID 520978 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-3077e5dedc51470f9a0c8e2e365e3f6d
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

Loading…