Triacetoxyperiodinane → HCID 117729319, compound

HRID 2200029Notes

Reaction equation

HRID 2200029 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:19][OH:20])[CH:5]=[C:6]([Cl:18])[C:7]=1[C:8]1[N:12]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:18][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]1[N:12]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1)[CH:19]=[O:20]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 117729102HCID 117729102, compound

Product 1

HCID 117729319HCID 117729319, compoundYield 118.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of Intermediate 13b (0.57 g, 1.80 mmol) in DCM (18 mL) at 0° C. was treated with Dess Martin periodinane (0.85 g, 2.00 mmol) and the solution was stirred at 0° C. for 1 h. The mixture was diluted with a saturated aqueous sodium bicarbonate solution and the layers were separated. The aqueous layer was then extracted with DCM (2×). The combined organic layers were washed with a saturated aqueous sodium bicarbonate solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was dissolved in DCM containing a few drops of MeOH and purified by FCC, using 0-5% MeOH in DCM, to give the title compound (0.66 g, quant). LCMS (Method 3): Rt 3.03 min, m/z 328, 330 [MH+].

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was then extracted with DCM (2×)
  3. washThe combined organic layers were washed with a saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in DCM containing a few drops of MeOH
  8. custompurified by FCC

Sources & evidence

ORD record
ord-d7e89a0aab53403893987fbfe9962c89
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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