Iodine → HCID 12773673, compound

HRID 848461Notes

Reaction equation

HRID 848461 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. dry with materialThe organic layer is dried (MgSO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-45f1f3051d7c445688d6e49e13d1b640
Source dataset
uspto-grants-1981_10
Patent number
US04296113

Reaction notes

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