Triacetoxyperiodinane → HCID 58316934, compound

HRID 1187288Notes

Reaction equation

HRID 1187288 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([CH:18]([C:20]2[C:28]3[C:27]([Cl:29])=[N:26][CH:25]=[N:24][C:23]=3[N:22]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[CH:21]=2)[OH:19])[C:12]=1[F:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[CH2:1]([O:8][C:9](=[O:41])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([C:20]2[C:28]3[C:27]([Cl:29])=[N:26][CH:25]=[N:24][C:23]=3[N:22]([S:30]([C:33]3[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=3)(=[O:32])=[O:31])[CH:21]=2)=[O:19])[C:12]=1[F:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 58316916HCID 58316916, compound

Product 1

HCID 58316934HCID 58316934, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a round bottom flask, (3-{[4-chloro-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-hydroxy-methyl}-2,4-difluoro-phenyl)-carbamic acid benzyl ester (34, 311 mg, 0.519 mmol) is dissolved in 35 mL of tetrahydrofuran and Dess-Martin periodinane (242 mg, 0.571 mmol) is added. The resulting mixture is stirred at room temperature, and additional Dess-Martin periodinane is added. After 60 minutes, the reaction is quenched with water and extracted with ethyl acetate. The organic layer is washed with aqueous sodium bicarbonate, then brine, and dried with magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified by silica gel chromatography eluting with ethyl acetate and hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (35, 152 mg). MS (ESI) [M+H+]+=596.8.

Workup

  1. customthe reaction is quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with aqueous sodium bicarbonate
  4. dry with materialbrine, and dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under vacuum
  7. customThe resulting material is purified by silica gel chromatography
  8. washeluting with ethyl acetate and hexane
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-488b60e90a8d4654b55b9c33bea5cf54
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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