N-Iodosuccinimide → HCID 117677347, compound

HRID 1507491Notes

Reaction equation

HRID 1507491 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([S:9][CH3:10])[N:6]=[C:5]([NH:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)[CH:4]=1.C1C(=O)N([I:32])C(=O)C1>CC#N>[I:32][C:4]1[C:5]([NH:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[N:6][C:7]([S:9][CH3:10])=[N:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 89554205HCID 89554205, compound

Product 1

HCID 117677347HCID 117677347, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 18 (1.00 g, 2.82 mmol) was dissolved in MeCN (50 mL) and NIS (952 mg, 4.23 mmol) was added and the reaction was heated to reflux for 1 h. The solution was concentrated and the residue was dissolved in EtOAc, wash with a saturated aqueous solution of NaHCO3 and a saturated aqueous solution of NaS2O3, dried (MgSO4), filtered and concentrated to give the title compound as a light yellow solid. LCMS 2.06 min, 481 (M+H)

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1 h
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwash with a saturated aqueous solution of NaHCO3
  6. dry with materiala saturated aqueous solution of NaS2O3, dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0626bdd4b3d24670a06b9e8d846cfd31
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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