Triacetoxyperiodinane → HCID 58192809, compound

HRID 2092651Notes

Reaction equation

HRID 2092651 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH:9]1[OH:18])[CH2:15]2)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[C:9]1=[O:18])[CH2:15]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58192788HCID 58192788, compound

Product 1

HCID 58192809HCID 58192809, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 20B (500 mg, 1.87 mmol) in 10 mL of DCM was added Dess martin periodinane (1.03 g, 3 mmol) at one portion at rt. The mixture was stirred at rt overnight and was quenched by 20 mL of NH4Cl aq (Sat'd) solution. The mixture was extracted by DCM (5 mL×3) and the combined DCM layers were dried over Na2SO4. Solvent was remove under vacuum and the residue was purified by silica gel chromatography (Hexane:EtOAc 2:1(v/v)) to give the title compounds (20C) (510 mg, 90%). LC-MS (ESR): m/z=266 (M+H)+.

Workup

  1. customwas quenched by 20 mL of NH4Cl aq (Sat'd) solution
  2. extractionThe mixture was extracted by DCM (5 mL×3)
  3. dry with materialthe combined DCM layers were dried over Na2SO4
  4. customSolvent was remove under vacuum
  5. customthe residue was purified by silica gel chromatography (Hexane:EtOAc 2:1(v/v))

Sources & evidence

ORD record
ord-523789d9ad38421595c156ed32567cea
Source dataset
uspto-grants-2013_05
Patent number
US08440720B2

Reaction notes

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