Tetrahydrofuran → HCID 9951913, compound

HRID 583931Notes

Reaction equation

HRID 583931 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH3:25])[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)(=[O:11])=[O:10])=[CH:5][C:4]=1[N+:26]([O-])=O.C1COCC1>CO.[Pd]>[NH2:26][C:4]1[CH:5]=[C:6]([S:9]([N:12]([CH3:25])[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)(=[O:10])=[O:11])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 22344731HCID 22344731, compound

Product 1

HCID 9951913HCID 9951913, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 52A (00 mg) in methanol:THF (1 mL:1 mL) was treated with 10% palladium on carbon, stirred under hydrogen (1 atm) for 4 hours, filtered through diatomaceous earth (Celite®), and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2% methanol/dichloromethane to provide 31 mg of the desired product.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-57249030c4854405b7a86772840cfb4d
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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