Iodine → HCID 89501073, compound

HRID 1467809Notes

Reaction equation

HRID 1467809 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][C:17]([CH3:25])([CH3:24])[NH:18][CH2:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].II.CC([O-])=O.[Na+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][C:17]([CH3:25])([CH3:24])[N:18]=[CH:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 807IodineHCID 517045Sodium AcetateHCID 117600738HCID 117600738, compound

Product 1

HCID 89501073HCID 89501073, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 78C (170 mg, 0.49 mmol) in EtOH (2 mL) was added iodine (281 mg, 2.21 mmol) and NaOAc (60 mg, 0.73 mmol) and the reaction mixture was heated to 80° C. After 3 h, the solvent was evaporated and the residue was quenched with 10% sodium thiosulphate solution and extracted twice with EtOAc and the combined organics were washed with H2O. The organic layer was extracted with 2 mL of 0.5 N HCl solution and the combined aqueous layers were basified with ammonia solution and extracted with EtOAc twice. The combined organics were washed with H2O, brine and dried over Na2SO4, filtered and concentrated to give 78D (90 mg, 53.2%). MS (ESI) m/z: 344.2 (M+H)+.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was quenched with 10% sodium thiosulphate solution
  3. extractionextracted twice with EtOAc
  4. washthe combined organics were washed with H2O
  5. extractionThe organic layer was extracted with 2 mL of 0.5 N HCl solution
  6. extractionextracted with EtOAc twice
  7. washThe combined organics were washed with H2O, brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bf0693947e2044f5a50add4a4eb3177d
Source dataset
uspto-grants-2015_04
Patent number
US09000172B2

Reaction notes

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