Potassium Persulfate → HCID 54434479, compound

HRID 1032930Notes

Reaction equation

HRID 1032930 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([F:26])=[CH:10][C:11]3[C:21](=[O:22])[C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:13]4[C@@H:14]([CH3:18])[CH2:15][S:16][C:17]=2[C:12]=34)[CH:5]=[C:4]([CH3:27])[N:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:29].[K+].[K+].S([O-])(O)(=O)=O.[K+].S([O-])([O-])(=O)=O.[K+].[K+]>C(O)(=O)CC>[CH3:27][C:4]1[CH:5]=[C:6]([C:8]2[C:9]([F:26])=[CH:10][C:11]3[C:21](=[O:22])[C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:13]4[CH:14]([CH3:18])[CH2:15][S@:16](=[O:29])[C:17]=2[C:12]=34)[CH:7]=[C:2]([CH3:1])[N:3]=1

Participants

6

Reactant 4

HCID 24412Potassium PersulfateHCID 24507Potassium SulfateHCID 129581Win 58161HCID 516920Potassium bisulfate

Product 1

HCID 54434479HCID 54434479, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

(S)-10-(2,6-Dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6-carboxylic acid (U.S. Pat. No. 4,839,355, Example 7f) (192 mg) and 153.7 mg of a mixture of potassium monopersulfate, potassium hydrogen sulfate and potassium sulfate (mole ratio 2:1:1) (Oxone®) (0.5 mM of potassium monopersulfate) in 20 ml of aqueous propionic acid (20% water) were combined at 0° C. with stirring. The mixture was allowed to come to room temperature, stirred for 4 hours and concentrated to dryness. Saturated sodium chloride solution was added to the mixture which was then extracted with chloroform. The chloroform extract was dried over sodium sulfate and concentrated to dryness. The resulting residue was treated with ethyl alcohol to give 60 mg (30% yield) of the title compound as a solid which was collected by filtration; m.p. 294.0°-295.0° C.

Workup

  1. customwere combined at 0° C.
  2. customto come to room temperature
  3. stirringstirred for 4 hours
  4. concentrationconcentrated to dryness
  5. additionSaturated sodium chloride solution was added to the mixture which
  6. extractionwas then extracted with chloroform
  7. extractionThe chloroform extract
  8. dry with materialwas dried over sodium sulfate
  9. concentrationconcentrated to dryness
  10. additionThe resulting residue was treated with ethyl alcohol

Sources & evidence

ORD record
ord-29c845f293d345f4a7fe649c693d9a14
Source dataset
uspto-grants-1994_05
Patent number
US05308843

Reaction notes

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