Sodium Iodide → HCID 67043644, compound

HRID 601780Notes

Reaction equation

HRID 601780 reaction equation
[CH3:1][N:2]([CH3:43])[C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]1([C:35]2[C:36]([O:41]C)=[N:37][CH:38]=[CH:39][CH:40]=2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[N:13]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])(=[O:23])=[O:22])[C:12]1=[O:34])=[O:4].[I-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[CH3:43][N:2]([CH3:1])[C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]1([C:35]2[C:36](=[O:41])[NH:37][CH:38]=[CH:39][CH:40]=2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[N:13]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])(=[O:22])=[O:23])[C:12]1=[O:34])=[O:4]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 11319623HCID 11319623, compound

Product 1

HCID 67043644HCID 67043644, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of example 5 (0.16 mmol, 100 mg) and sodium iodide (0.32 mmol, 109 mg) in acetic acid (1 mL) was heated overnight at 40° C. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium dithionate solution, water and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo. Chromatographic purification over silica gel (gradient from 4% to 12% MeOH in dichloromethane) yielded 59 mg (60%) of a white crystalline solid.

Workup

  1. washwashed with aqueous sodium dithionate solution, water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customChromatographic purification over silica gel (gradient from 4% to 12% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-2c4009d4b6ed4e05a7f37c0f51598b09
Source dataset
uspto-grants-2011_03
Patent number
US07902379B2

Reaction notes

Loading…