Triacetoxyperiodinane → HCID 86666002, compound

HRID 1808796Notes

Reaction equation

HRID 1808796 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:39]=[CH:38][C:27]([C:28]([N:30]([C@@H:32]([CH:35]([CH3:37])[CH3:36])[CH2:33][OH:34])[CH3:31])=[O:29])=[CH:26][C:25]=1[CH3:40].C([O-])(O)=O.[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[F:23][C:24]1[CH:39]=[CH:38][C:27]([C:28]([N:30]([CH3:31])[C@@H:32]([CH:35]([CH3:36])[CH3:37])[CH:33]=[O:34])=[O:29])=[CH:26][C:25]=1[CH3:40]

Participants

6

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 656671Sodium PyrosulfiteHCID 67773353HCID 67773353, compound2×

Product 1

HCID 86666002HCID 86666002, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (0.25 g, 0.59 mmol) was added to (S)-4-fluoro-N-(1-hydroxy-3-methylbutan-2-yl)-N,3-dimethylbenzamide (Compound Z) (0.1 g, 0.39 mmol) in DCM (3 mL) at rt. The resultant mixture was stirred at rt for 2 h. An aqueous NaHCO3 (8 wt %) solution containing sodium pyrosulphite (0.059 mL, 0.43 mmol) was added and the resultant mixture was stirred vigorously for 15 min. The organic phases was washed with Na2CO3 (8 wt %), filtered through a phase separator and dried using Na2SO4. The solvent was removed under reduced pressure to give the title compound (93 mg, 94%). The obtained crude product was used without further purification. LCMS (M+H)+: 252.

Workup

  1. additionwas added
  2. washThe organic phases was washed with Na2CO3 (8 wt %)
  3. filtrationfiltered through a phase separator
  4. customdried
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1ad8cd91e0ff42aa8389d20c34606ddf
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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