Triacetoxyperiodinane → HCID 42610411, compound

HRID 215781Notes

Reaction equation

HRID 215781 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:28][CH2:29][OH:30])[C:5]([C:7]1[CH:8]=[N:9][N:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C@H:23]3[CH3:27])=[CH:14][CH:13]=2)[CH:11]=1)=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)(Cl)Cl.O>[OH:1][CH:2]1[O:30][CH2:29][CH2:28][N:4]([C:5]([C:7]2[CH:8]=[N:9][N:10]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:26][CH2:25][CH2:24][C@H:23]4[CH3:27])=[CH:16][CH:17]=3)[CH:11]=2)=[O:6])[CH2:3]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 42610554HCID 42610554, compound

Product 1

HCID 42610411HCID 42610411, compoundYield 2.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazole-4-carboxylic acid bis-(2-hydroxyethyl)-amide obtained in Example 20 (1.0 g) in chloroform (8 mL), Dess-Martin reagent (1.1 g) was added and stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with chloroform. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=4:1) and further purified by preparative TLC (1 mm thickness, developing solvent: chloroform:methanol=9:1) to give the titled compound (0.022 g) as a colorless amorphous substance.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=4:1)
  6. customfurther purified by preparative TLC (1 mm thickness, developing solvent: chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-5aac90aefd0c4cc5ad3a465047c381d7
Source dataset
uspto-grants-2012_06
Patent number
US08193176B2

Reaction notes

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