HCID 22033137, compound → HCID 22033384, compound

HRID 1792323Notes

Reaction equation

HRID 1792323 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH2:29][CH2:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])[C:7]([CH3:18])([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[CH2:8][O:9]2)=[CH:4][CH:3]=1.[OH:39]OS([O-])=O.[K+]>O1CCCC1.O>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28]([CH2:29][CH2:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:36])([F:34])[F:35])=[O:39])[C:7]([CH3:18])([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)[CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 22033137HCID 22033137, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22033384HCID 22033384, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3RS,4RS)-7-hydroxy-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]-3-(4-pyridyl)chroman (6.1 mg, 0.011 mmol) in tetrahydrofuran (0.5 ml) was added under ice-cooling a solution of Oxone® (monopersulfate compound; DuPont product) (3.4 mg, 0.0055 mmol) in water (0.5 ml), which was then stirred for 5 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate and washed with saturated saline solution. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate) to give (3RS,4RS)-7-hydroxy-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-3-(4-pyridyl)chroman (5.1 mg, yield 81%).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washwashed with saturated saline solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2ba87f94156c4f3bb435ba83a2a70596
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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