Triacetoxyperiodinane → HCID 86732269, compound

HRID 930433Notes

Reaction equation

HRID 930433 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:9]([NH:14][S@@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])([CH2:11][CH2:12][OH:13])[CH3:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>O.C(Cl)Cl>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:9]([NH:14][S@@:15]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:16])([CH2:11][CH:12]=[O:13])[CH3:10]

Participants

6

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86732270HCID 86732270, compound

Product 1

HCID 86732269HCID 86732269, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (R)-N-((S)-2-(2-chloro-3-fluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide (9.30 g, 28.9 mmol), dichloromethane (150 mL) and dess-martin periodinane (14.22 g, 33.5 mmol) was stirred at rt for 1 h. The mixture was diluted with water (150 mL), DCM and sodium bicarbonate (12.14 g, 144 mmol). The mixture was filtered through celite. The aqueous layer was extracted with DCM. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude was purified by silica gel chromatography: 240 g, 5-25% EtOAc-hexane in 5 min, 25-80% in 20 min to give (R)-N-((S)-2-(2-chloro-3-fluorophenyl)-4-oxobutan-2-yl)-2-methylpropane-2-sulfinamide as yellow oil (8.98 g, 97%). MS m/z=320 [M+H]+. Calculated for C14H19ClFNO2S: 319.8.

Workup

  1. filtrationThe mixture was filtered through celite
  2. extractionThe aqueous layer was extracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by silica gel chromatography
  8. wait240 g, 5-25% EtOAc-hexane in 5 min

Sources & evidence

ORD record
ord-1be21a76c1994a388c89ef2e740727f9
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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