Triacetoxyperiodinane → HCID 44469404, compound

HRID 1690009Notes

Reaction equation

HRID 1690009 reaction equation
[F:1][C:2]1[C:7]([CH:8]([OH:18])[C:9]2[C:17]3[CH:16]=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[C:6]([F:19])[CH:5]=[CH:4][C:3]=1[NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[CH:16]=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)=[O:18])=[C:6]([F:19])[CH:5]=[CH:4][C:3]=1[NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57963266HCID 57963266, compound

Product 1

HCID 44469404HCID 44469404, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-1-sulfonic acid 2,4-difluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl-amide (P-0001, 0.150 g, 0.392 mmol), 3 mL of tetrahydrofuran was added, followed by Dess-Martin periodinane (0.166 g, 0.392 mmol). The reaction was allowed to stir at room temperature for 1 hour, then the reaction was extracted with ethyl acetate and 5:1 saturated sodium bicarbonate:saturated sodium thiosulfate. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with a gradient of 1 to 5% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum to give the desired compound (P-0002, 110 mg). MS(ESI)[M+H+]+=381.2. LC/MS indicated 97.0% purity.

Workup

  1. extractionthe reaction was extracted with ethyl acetate and 5:1 saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with a gradient of 1 to 5% methanol in dichloromethane
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f94d9ad4e34e42708799f62e9c511397
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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