Sodium Iodide → HCID 23387351, compound

HRID 1790769Notes

Reaction equation

HRID 1790769 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 CH2Cl2 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 CH2Cl2
  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-efe6847848e54281b6087f19f3eb7e69
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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