N-Iodosuccinimide → HCID 178519297, compound

HRID 2377261Notes

Reaction equation

HRID 2377261 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[CH:3]=[N:2]1)=[CH:10][C:9]([CH:13]=[O:14])=[CH:8][CH:7]=3.[I:15]N1C(=O)CCC1=O>CN(C)C=O>[I:15][C:3]1[C:4]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH:13]=[O:14])[CH:10]=3)[C:5]=2[NH:1][N:2]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 59644137HCID 59644137, compound

Product 1

HCID 178519297HCID 178519297, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 316 (2.13 g, 11.6 mmol) and N-iodosuccinimide (3.13 g, 13.9 mmol) in N,N-dimethylformamide (45 mL) was heated to about 80° C. for about 5 hours. The reaction mixture was cooled to room temperature and was concentrated in high vacuum. The residue was partitioned between water and ethyl acetate, the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (2:1) as eluent to provide the desired product. MS (ESI): m/z 309 (M−H)−.

Workup

  1. concentrationwas concentrated in high vacuum
  2. customThe residue was partitioned between water and ethyl acetate
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-35380c8db9c542f18104b5c6e1aae064
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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