Potassium Carbonate → HCID 135627639, compound

HRID 643936Notes

Reaction equation

HRID 643936 reaction equation
[CH2:1]([O:4][C:5]1[C:9]2[CH:10]=[C:11]([N:18]3[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:25])[CH2:19]3)[C:12]([O:14]CC=C)=[CH:13][C:8]=2[O:7][N:6]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+]>CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:4][C:5]1[C:9]2[CH:10]=[C:11]([N:18]3[S:22](=[O:23])(=[O:24])[NH:21][C:20](=[O:25])[CH2:19]3)[C:12]([OH:14])=[CH:13][C:8]=2[O:7][N:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 66750664HCID 66750664, compound

Product 1

HCID 135627639HCID 135627639, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-(3,6-bis-allyloxybenzo[d]isoxazol-5-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (0.055 g, 0.15 mmol) in EtOH (4 mL) is added tetrakis(triphenylphosphine)palladium(0) (0.005 g, 0.004 mmol). The mixture is stirred for 5 min at room temperature, at which point potassium carbonate (0.056 g, 0.405 mmol) is added. The mixture is stirred at room temperature for 5.5 h. The solvent is removed under reduced pressure and the crude product is purified by chromatography on a Biotage purification system eluting with a gradient of water/CH3CN to afford 5-(3-allyloxy-6-hydroxybenzo[d]isoxazol-5-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a solid: (M−H)−=324.0.

Workup

  1. additionis added
  2. customThe solvent is removed under reduced pressure
  3. customthe crude product is purified by chromatography on a Biotage purification system
  4. washeluting with a gradient of water/CH3CN

Sources & evidence

ORD record
ord-522641528ac442abaaeff161a4c8a8d2
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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