N-Iodosuccinimide → HCID 89498954, compound

HRID 588660Notes

Reaction equation

HRID 588660 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-1fa7b7fc710b467da6803fb0fa4d5d62
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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