Triacetoxyperiodinane → HCID 86732105, compound

HRID 930277Notes

Reaction equation

HRID 930277 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@@:8]([NH:14][S@@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])([CH2:11][CH2:12][OH:13])[CH2:9][F:10])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@@:8]([NH:14][S@@:15]([C:17]([CH3:19])([CH3:18])[CH3:20])=[O:16])([CH2:11][CH:12]=[O:13])[CH2:9][F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86732104HCID 86732104, compound

Product 1

HCID 86732105HCID 86732105, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-N-((S)-2-(5-bromo-2-fluorophenyl)-1-fluoro-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide (4.84 g, 12.59 mmol, step 4) in DCM (100 ml) was added Dess-martin periodinane (5.88 g, 13.85 mmol, Aldrich) at RT. The reaction was stirred for 2.5 hours. The reaction was quenched with water, followed by the addition of aqueous, saturated sodium bicarbonate solution, and DCM. The organic layer was washed with sequentially with saturated sodium bicarbonate solution three times and brine before drying over magnesium sulfate and concentrating under reduced pressure. The crude residue was purified via silica gel flash chromatography using a gradient of 10-60% acetone in hexanes to afford the title compound as a clear oil (4.04 g, 10.58 mmol, 84% yield). MS m/z=382.0 M+. Calculated for C14H18BrF2NO2S: 382.264

Workup

  1. customThe reaction was quenched with water
  2. additionfollowed by the addition of aqueous, saturated sodium bicarbonate solution, and DCM
  3. washThe organic layer was washed with sequentially with saturated sodium bicarbonate solution three times and brine
  4. dry with materialbefore drying over magnesium sulfate
  5. concentrationconcentrating under reduced pressure
  6. customThe crude residue was purified via silica gel flash chromatography

Sources & evidence

ORD record
ord-af35b4a9895e4f2398abc4be191aaf84
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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