Iodine → HCID 12773673, compound

HRID 1065669Notes

Reaction equation

HRID 1065669 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:13][C:12](=[O:14])[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5].[OH-:15].[Na+].II>O.C(O)C>[O:15]=[C:4]([N:6]1[CH2:13][C:12](=[O:14])[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])[CH2:3][CH2:2][S:1][S:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:13][C:12](=[O:14])[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5]

Participants

6

Reactant 3

HCID 807IodineHCID 14798Sodium Hydroxide2×HCID 12773665HCID 12773665, compound

Product 1

HCID 12773673HCID 12773673, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The product from Example 2 is dissolved in water and the pH adjusted to 6.5 by the addition of 1 N sodium hydroxide. To this stirred solution is added dropwise a 0.5 M iodine solution in 95% ethanol (6.34 g. iodine/50 ml. solution) while maintaining the pH at 5.5 to 6.5 with 1 N sodium hydroxide. Excess iodine is removed with dilute sodium thiosulfate and the solution is concentrated, cooled and acidified with 1:1 hydrochloric acid. Solvent is added and the layers are separated. The organic layer is dried MgSO4) and the solvent evaporated to yield as a residue 1,1'-[dithiobis(1-oxo-3,1-propanediyl)]bis[4-oxo-L-proline].

Workup

  1. customExcess iodine is removed with dilute sodium thiosulfate
  2. concentrationthe solution is concentrated
  3. temperaturecooled
  4. additionSolvent is added
  5. customthe layers are separated
  6. customevaporated

Sources & evidence

ORD record
ord-0765431721b049e2bea441c118541c32
Source dataset
uspto-grants-1982_05
Patent number
US04330548

Reaction notes

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