m-Chloroperbenzoic acid → HCID 86691003, compound

HRID 520983Notes

Reaction equation

HRID 520983 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]([N:13]([CH2:15][CH3:16])[CH3:14])=[O:12])=[C:4]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[F:28])(=[O:20])=[O:19])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:37])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:9][CH2:10][C:11]([N:13]([CH2:15][CH3:16])[CH3:14])=[O:12])=[O:37])=[C:4]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[F:28])(=[O:20])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 866910023-[(4-chloro-2-{[(4-chloro-2-fluorophenyl)sulfonyl]amino}phenyl)sulfanyl]-N-ethyl-N-methylpropanamide

Product 1

HCID 86691003HCID 86691003, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(4-chloro-2-{[(4-chloro-2-fluorophenyl)sulfonyl]amino}phenyl)sulfanyl]-N-ethyl-N-methylpropanamide (119 mg, 0.256 mmol) in CH2Cl2 (5 ml) was added mCPBA (61 mg, ˜0.26 mmol). The reaction was stirred at room temperature for 1 hour and was concentrated. The residue was purified by flash column chromatography on silica gel (50-100% EtOAc in hexane, then 10% MeOH in CH2Cl2) to yield the title compound (53 mg, 43%) as a mixture of amide bond cis-trans isomers.

Workup

  1. concentrationwas concentrated
  2. customThe residue was purified by flash column chromatography on silica gel (50-100% EtOAc in hexane

Sources & evidence

ORD record
ord-e4d133b7d00f4e10bd97f6e6db453745
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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