Iodine → HCID 86738301, compound

HRID 2059076Notes

Reaction equation

HRID 2059076 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([N:6]1[C@H:10]([C:11]([OH:13])=[O:12])[C@@H:9]([CH3:14])[O:8][CH2:7]1)=[O:5].[OH-:15].[Na+].II>O.C(O)C>[O:15]=[C:4]([N:6]1[C@H:10]([C:11]([OH:13])=[O:12])[C@H:9]([CH3:14])[O:8][CH2:7]1)[CH2:3][CH2:2][S:1][S:1][CH2:2][CH2:3][C:4]([N:6]1[CH:10]([C:11]([OH:13])=[O:12])[CH:9]([CH3:14])[O:8][CH2:7]1)=[O:5]

Participants

6

Reactant 3

HCID 807IodineHCID 14798Sodium Hydroxide2×HCID 12831220HCID 12831220, compound

Product 1

HCID 86738301HCID 86738301, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(4S-trans)-3-(3-Mercapto-1-oxopropyl)-5-methyl-4-oxazolidinecarboxylic acid from Example 1 is dissolved in water and the pH is adjusted to about 6.5 with 1 N sodium hydroxide. To this stirred solution is added dropwise 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 from the reaction mixture with dilute sodium thiosulfate and the solution is then concentrated, cooled and acidified with 1:1 hydrochloric acid. Solvent is added and the mixture is saturated with sodium chloride, stirred, and the layers separated. The organic layer is dried and the solvent evaporated to yield (S,S)-3,3'-[dithiobis(1-oxo-3,1-propanediyl)]bis[5-methyl-4-oxazolidinecarboxylic acid].

Workup

  1. customExcess iodine is removed from the reaction mixture with dilute sodium thiosulfate
  2. concentrationthe solution is then concentrated
  3. temperaturecooled
  4. additionSolvent is added
  5. customthe layers separated
  6. customThe organic layer is dried
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-fbe7ca6f92f548b7ac8fcb22991d25b5
Source dataset
uspto-grants-1982_03
Patent number
US04321392

Reaction notes

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