Water → HCID 59506304, compound

HRID 1098757Notes

Reaction equation

HRID 1098757 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([S:7][C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][C:9]=2[C:17]([F:20])([F:19])[F:18])=[CH:3][CH:2]=1.[OH:21]OS([O-])=O.[K+].[OH2:27]>CO.O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([S:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][C:9]=2[C:17]([F:18])([F:20])[F:19])(=[O:21])=[O:27])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 59506128HCID 59506128, compound

Product 1

HCID 59506304HCID 59506304, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product obtained from step 2 (4.80 g, 16.15 mmol) in methanol (80 ml) and tetrahydrofurane (80 ml) was added drop wise to a solution of oxone, monopersulfate compound (17.87 g, 29.07 mmol) in water (80 ml) at 0° C. The suspension was stirred 4 days at RT. Water (100 ml) was added and the reaction mixture was extracted with DCM. The combined organic phases were washed with brine and dried over magnesium sulphate. Evaporation and purification of the crude product by silica gel chromatography using DCM/methanol=20:1 gave the desired product (2.80 g, 53%).

Workup

  1. extractionthe reaction mixture was extracted with DCM
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customEvaporation and purification of the crude product by silica gel chromatography

Sources & evidence

ORD record
ord-279e1d7634df431fa763282a64206536
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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