Sodium Iodide → HCID 23387351, compound

HRID 489017Notes

Reaction equation

HRID 489017 reaction equation
[C:1](=[O:26])([O:23][CH2:24]Cl)[O:2][CH2:3][CH2:4][O:5][C:6](=[O:22])[C@H:7]([CH:19]([CH3:21])[CH3:20])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[I-:27].[Na+]>C(#N)C>[C:1](=[O:26])([O:23][CH2:24][I:27])[O:2][CH2:3][CH2:4][O:5][C:6](=[O:22])[C@H:7]([CH:19]([CH3:21])[CH3:20])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 23387518HCID 23387518, compound

Product 1

HCID 23387351HCID 23387351, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(N-CBz-L-valyloxy)-ethyl chloromethyl carbonate (3.88 g, 10 mmol) in acetonitrile (50 mL), was added sodium iodide (7.50 g, 50 mmol). The solution was stirred for 4 h at 60° C. The resulting suspension was filtered and the filtrate was evaporated. The residue was dissolved in CH1Cl2 and washed with aqueous sodium thiosulfate (0.1 M). The organic phase was dried (Na2SO4) and concentrated under reduced pressure, to give 4.51 g 2-(N-CBz-L-valyloxy)-ethyl iodomethyl carbonate.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in CH1Cl2
  4. washwashed with aqueous sodium thiosulfate (0.1 M)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a336c0b151ba44e1a0d3ea089ac92734
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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