Triacetoxyperiodinane → HCID 57901681, compound

HRID 1851622Notes

Reaction equation

HRID 1851622 reaction equation
[OH:1][CH:2]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[S:9]([N:12]([CH3:27])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]1[S:23][CH:24]=[CH:25][N:26]=1)=[CH:18]2)(=[O:11])=[O:10])[CH3:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+]>C(#N)C>[C:2]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[S:9]([N:12]([CH3:27])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]1[S:23][CH:24]=[CH:25][N:26]=1)=[CH:18]2)(=[O:11])=[O:10])(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57901750HCID 57901750, compound

Product 1

HCID 57901681HCID 57901681, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(1-hydroxyethyl)-N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-3-sulfonamide (180 mg) in acetonitrile (10 mL) was added Dess-Martin reagent (212 mg), and the mixture was stirred at room temperature for 16 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (153 mg, yield 87%) as white crystals. melting point 156° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e7acde48384a49718501cf1c561baf25
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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