N-Iodosuccinimide → HCID 89498954, compound

HRID 336583Notes

Reaction equation

HRID 336583 reaction equation
[CH3:1][O:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([CH2:13][N:14]4[C:18]([CH3:19])=[CH:17][CH:16]=[N:15]4)([CH2:6]3)[CH2:4]1)[CH2:10]2.[I:20]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[I:20][C:17]1[CH:16]=[N:15][N:14]([CH2:13][C:5]23[CH2:6][CH:7]4[CH2:8][CH:9]([CH2:10][C:3]([O:2][CH3:1])([CH2:12]4)[CH2:4]2)[CH2:11]3)[C:18]=1[CH3:19]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 89499055HCID 89499055, compound

Product 1

HCID 89498954HCID 89498954, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of EXAMPLE 16D (0.116 g) and N-iodosuccinimide (0.11 g) in 1 mL DMF was stirred overnight. The mixture was taken up in ethyl acetate, and the resulting solution was washed three times with water, and brine, then dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel with 0-50% ethyl acetate/hexanes to provide the title compound.

Workup

  1. washthe resulting solution was washed three times with water, and brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel with 0-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-95f1e57d15b3487f88956a473c9e658d
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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