Triacetoxyperiodinane → HCID 57955235, compound

HRID 73695Notes

Reaction equation

HRID 73695 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[NH2:23][C:24]1[C:29]2=[C:30]([C:42]3[CH:47]=[CH:46][C:45]([NH:48][C:49]([NH:51][C:52]4[CH:57]=[C:56]([C:58]([F:61])([F:60])[F:59])[CH:55]=[CH:54][N:53]=4)=[O:50])=[CH:44][CH:43]=3)[C:31]([CH2:40][OH:41])=[C:32]([CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[N:28]2[N:27]=[CH:26][N:25]=1>CS(C)=O.CCOC(C)=O>[NH2:23][C:24]1[C:29]2=[C:30]([C:42]3[CH:43]=[CH:44][C:45]([NH:48][C:49]([NH:51][C:52]4[CH:57]=[C:56]([C:58]([F:60])([F:61])[F:59])[CH:55]=[CH:54][N:53]=4)=[O:50])=[CH:46][CH:47]=3)[C:31]([CH:40]=[O:41])=[C:32]([CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[N:28]2[N:27]=[CH:26][N:25]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57955272HCID 57955272, compound

Product 1

HCID 57955235HCID 57955235, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dess-Martin periodinane (703.6 mg, 1.66 mmol) was added to a stirring solution of Example 62 (600 mg, 1.11 mmol) dissolved in DMSO (3 mL). After 1 hour HPLC indicated that the reaction was complete. The reaction was diluted with EtOAc (200 mL) washed with aq. Sodium thiosulfate solution (2M) (2×), and saturated NaHCO3 solution (2×). The organic layer was dried (Na2SO4) and concentrated to give a brown powder which was triturated with 10% Et2O/Hexanes to afford 450 mg (0.83 mmol, 75.3%) of the title compound. 1H-NMR (DMSO-d6). δ 10.00 (s, 1H), 9.95 (s, 1H), 9.84 (s, 1H), 8.60 (d, J=5.4 Hz, 1H), 8.12 (s, 1H), 8.07 (s, 1H), 7.89 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.43 (d, J=5.1 Hz, 1H), 4.18 (s, 2H), 3.57-3.54 (m, 4H), 2.55-2.51 MS [M+H]+=541; LCMS RT=2.50 min.

Workup

  1. washwashed with aq. Sodium thiosulfate solution (2M) (2×), and saturated NaHCO3 solution (2×)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give a brown powder which
  5. customwas triturated with 10% Et2O/Hexanes

Sources & evidence

ORD record
ord-2cd400576e2d4d6891d47426ed716825
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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