Water → HCID 90202333, compound

HRID 929766Notes

Reaction equation

HRID 929766 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]([NH2:16])=[O:15])[O:11][N:10]=2)=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>CS(C)=O>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:13]=[C:12]([C:14]([NH2:16])=[O:15])[O:11][N:10]=2)=[CH:7][CH:8]=1)=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 90202510HCID 90202510, compound2×

Product 1

HCID 90202333HCID 90202333, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-(4-hydroxymethyl-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 19; 100 mg, 0.46 mmol) in DMSO (1.5 mL) was added Dess-Martin periodinane (214 mg, 0.5 mmol). The mixture was stirred at room temperature for 2.5 h. Water (5 mL) was added and the mixture was filtered to give a white solid. The filtrate was extracted three times with EtOAc and the combined extracts were dried (Na2SO4), filtered and evaporated to give a residue. The white solid from the first filtration was triturated with MeOH and the mixture was filtered. The filtrate was evaporated to give a second residue. The two residues were combined and purified by chromatography (25% acetone/CH2Cl2) to give 3-(4-formyl-phenyl)-isoxazole-5-carboxylic acid amide (50 mg, 50%).

Workup

  1. filtrationthe mixture was filtered
  2. customto give a white solid
  3. extractionThe filtrate was extracted three times with EtOAc
  4. dry with materialthe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue
  8. filtrationThe white solid from the first filtration
  9. customwas triturated with MeOH
  10. filtrationthe mixture was filtered
  11. customThe filtrate was evaporated
  12. customto give a second residue
  13. custompurified by chromatography (25% acetone/CH2Cl2)

Sources & evidence

ORD record
ord-ffc0274662014c7ba982c65b8eca8a26
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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