m-Chloroperbenzoic acid → HCID 22712131, compound

HRID 352555Notes

Reaction equation

HRID 352555 reaction equation
[Cl:1][C:2]1[C:3]([F:25])=[N:4][C:5]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[C:6]([Cl:19])[C:7]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=1.ClC1C=C(C=CC=1)C(OO)=[O:31]>C(Cl)Cl>[Cl:19][C:6]1[C:5]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[N:4][C:3]([F:25])=[C:2]([Cl:1])[C:7]=1[S:8]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([CH3:17])[CH3:18])[CH:10]=1)=[O:31]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22712074HCID 22712074, compound

Product 1

HCID 22712131HCID 22712131, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dichloro-2-fluoro-4-(3-isopropyl-4-hydroxyphenylthio)-6-hydroxycarbonylmethylaminopyridine (25 mg, 0.06 mmol) in CH2Cl2 (1.5 mL) was added 3-chloroperoxy-benzoic acid (11 mg). The mixture was left to stir overnight (ca. 15 h) at ambient room temperature. The product was extracted with EtOAc (25 mL). The organic extract was washed with brine (25 mL), dried (Na2SO4), filtered and concentrated in vacuo. The isolated crude product was purified by preparative HPLC (from 50% B to 100% B for 10 min, Solvent A=90% H2O-10% MeOH-0.1% TFA Solvent B=10% MeOH-90% H2O-0.1% TFA, at 20 mL/min using column YMC ODS S5 20×100 mm) to afford 16.5 mg (64%) of title compound as a white solid.

Workup

  1. waitThe mixture was left
  2. extractionThe product was extracted with EtOAc (25 mL)
  3. extractionThe organic extract
  4. washwas washed with brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe isolated crude product
  9. customwas purified by preparative HPLC (from 50% B to 100% B for 10 min, Solvent A=90% H2O-10% MeOH-0.1% TFA Solvent B=10% MeOH-90% H2O-0.1% TFA, at 20 mL/min using column YMC ODS S5 20×100 mm)

Sources & evidence

ORD record
ord-a829e5220dcd4129ad730dc372fe40ef
Source dataset
uspto-grants-2004_06
Patent number
US06747048B2

Reaction notes

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