Sodium Iodide → HCID 12019884, compound

HRID 2186898Notes

Reaction equation

HRID 2186898 reaction equation
[C:1](=[O:18])([O:15][CH2:16]Cl)[O:2][C@H:3]([C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])[CH3:4].[I-:19].[Na+]>C(#N)C>[C:1](=[O:18])([O:15][CH2:16][I:19])[O:2][C@H:3]([C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])[CH3:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 69429312HCID 69429312, compound

Product 1

HCID 12019884HCID 12019884, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

[(1S)-1-(benzyloxycarbonyl)ethyl] chloromethyl carbonate (2.7 g) was dissolved in acetonitrile (4 ml) and sodium iodide (6.0 g) was added. The mixture was stirred at 60° C. for 2 hours under an argon atmosphere. After the reaction mixture was concentrated under reduced pressure, diethyl ether (100 ml) and water (100 ml) were added to the residue. The diethyl ether layer was separated and washed with an aqueous 5% sodium thiosulfate solution (80 ml), water (80 ml), and a saturated sodium chloride aqueous solution (80 ml) successively. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain [(1S)-1-(benzyloxycarbonyl)ethyl] iodomethyl carbonate (3.3 g) as a colorless liquid.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, diethyl ether (100 ml) and water (100 ml)
  2. additionwere added to the residue
  3. customThe diethyl ether layer was separated
  4. washwashed with an aqueous 5% sodium thiosulfate solution (80 ml), water (80 ml)
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-625784113c2a4572862448b1e975f0a5
Source dataset
uspto-grants-2002_06
Patent number
US06407129B1

Reaction notes

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