m-Chloroperbenzoic acid → 3-[(4-Chloro-2-{[(4-chloro-2-fluorophenyl)sulfonyl]amino}phenyl)sulfinyl]propanoic acid

HRID 520981Notes

Reaction equation

HRID 520981 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[C:4]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[F:25])(=[O:17])=[O:16])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1>C(Cl)Cl.CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:34])=[C:4]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[F:25])(=[O:17])=[O:16])[CH:3]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86690999HCID 86690999, compound

Product 1

HCID 866910013-[(4-Chloro-2-{[(4-chloro-2-fluorophenyl)sulfonyl]amino}phenyl)sulfinyl]propanoic acidYield 95.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(4-chloro-2-{[(4-chloro-2-fluorophenyl)sulfonyl]amino}phenyl)sulfanyl]propanoic acid (91 mg, 0.21 mmol) in CH2Cl2 (2 ml) and acetone (2 ml) was added mCPBA (50 mg, ˜0.21 mmol). The reaction was stirred at room temperature for 1 hour and was concentrated. The solid residue was rinsed with Et2O to yield the title compound (88 mg, 94%).

Workup

  1. concentrationwas concentrated
  2. washThe solid residue was rinsed with Et2O

Sources & evidence

ORD record
ord-ed6bce2198ab46c28626ff12540e24fd
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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