Triacetoxyperiodinane → HCID 71073378, compound

HRID 2408941Notes

Reaction equation

HRID 2408941 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1[C:35]2[CH:34]([CH2:36][O:37][C:38]([N:40]3[CH:44]=[CH:43][C:42]([NH:45][C:46](=[O:70])[CH:47]([C:49]4([NH:53][C:54](=[O:69])[CH:55]([NH:63][C:64]([O:66][CH2:67][CH3:68])=[O:65])[CH2:56][C:57]5([F:62])[CH2:61][CH2:60][CH2:59][CH2:58]5)[CH2:52][CH2:51][CH2:50]4)[OH:48])=[N:41]3)=[O:39])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1>ClCCCl>[CH:23]1[C:35]2[CH:34]([CH2:36][O:37][C:38]([N:40]3[CH:44]=[CH:43][C:42]([NH:45][C:46](=[O:70])[C:47]([C:49]4([NH:53][C:54](=[O:69])[CH:55]([NH:63][C:64]([O:66][CH2:67][CH3:68])=[O:65])[CH2:56][C:57]5([F:62])[CH2:61][CH2:60][CH2:59][CH2:58]5)[CH2:50][CH2:51][CH2:52]4)=[O:48])=[N:41]3)=[O:39])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 71073409HCID 71073409, compound

Product 1

HCID 71073378HCID 71073378, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Dess-Martin periodinane (47 mg, 0.11 mmol) was added to a solution of alcohol 58-a (0.079 mmol) in anh. DCE (3 ml). The reaction mixture was stirred at room temperature for 90 min and then quenched with 10% aq. Na2S2O3 and aq. NaHCO3 (sat.). The phases were separated and the organic layer was dried (Na2SO4) and concentrated. Purification by flash column chromatography (EtOAc/iso-Hexane, 0:100-40:60) gave the title compound (6.5 mg, 13%). MS m/z 660.1 (M+H)+.

Workup

  1. customquenched with 10% aq. Na2S2O3 and aq. NaHCO3 (sat.)
  2. customThe phases were separated
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (EtOAc/iso-Hexane, 0:100-40:60)

Sources & evidence

ORD record
ord-b683f6b35df14b85b9fd397929a2d2e0
Source dataset
uspto-grants-2014_08
Patent number
US08815809B2

Reaction notes

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