Water → HCID 135449000, compound

HRID 1290045Notes

Reaction equation

HRID 1290045 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[OH:13])[NH:9][C:8](=[O:14])[CH2:7]2)(=O)[CH3:2].[N:15]1C=CC=CC=1.O>CN(C)C=O>[CH3:2][C:1]1[C:4]2[CH:5]=[C:6]3[CH2:7][C:8](=[O:14])[NH:9][C:10]3=[CH:11][C:12]=2[O:13][N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 10352530HCID 10352530, compound

Product 1

HCID 135449000HCID 135449000, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the oxime acetate formed in step c (4.48 g, 18.0 mmol) and pyridine (14.6 mL, 180 mmol) in dimethylformamide (DMF) (660 mL) was heated at 125°-130° C. for 4 hours. The cooled reaction mixture was poured over water and extracted with EtOAc (4 times). The combined organic layer was washed with water and brine and dried (MgSO4), filtered, and concentrated. Purification by silica gel flash chromatography (50% EtOAc/hexanes→100% EtOAc) gave the title compound (2.20 g, 65%) as a pale yellow-orange solid.

Workup

  1. temperaturewas heated at 125°-130° C. for 4 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with EtOAc (4 times)
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel flash chromatography (50% EtOAc/hexanes→100% EtOAc)

Sources & evidence

ORD record
ord-30db1c9e8162453c9d7a65fb9426f055
Source dataset
uspto-grants-1998_05
Patent number
US05750542

Reaction notes

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