Sodium Iodide → HCID 23387355, compound

HRID 989983Notes

Reaction equation

HRID 989983 reaction equation
Cl[CH2:2][O:3][C:4]([NH:6][C:7]([CH3:28])([CH3:27])[CH2:8][O:9][C:10](=[O:26])[C@H:11]([CH:23]([CH3:25])[CH3:24])[NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:5].[I-:29].[Na+]>CC(C)=O>[I:29][CH2:2][O:3][C:4]([NH:6][C:7]([CH3:28])([CH3:27])[CH2:8][O:9][C:10](=[O:26])[C@H:11]([CH:23]([CH3:25])[CH3:24])[NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:5]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 56979540HCID 56979540, compound

Product 1

HCID 23387355HCID 23387355, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(N-(chloromethoxycarbonyl)-amino)-2-methyl-1-(N-benzyloxycarbonyl-L-valyloxy)propane (1.05 g, 2.53 mmole) in dry acetone (20 ml) was added sodium iodide (1.8 g, 12 mmole) and the mixture was stirred for 36 hours at room temperature. The mixture was evaporated under reduced pressure and ethyl acetate and water were added. The organic phase was washed with 10% sodium thiosulfate solution and water. The organic phase was dried with sodium sulfate and evaporated under reduced pressure. Yield: 1.04 g=81%

Workup

  1. customThe mixture was evaporated under reduced pressure and ethyl acetate and water
  2. additionwere added
  3. washThe organic phase was washed with 10% sodium thiosulfate solution and water
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9e6aaccab92c466f8bdf0e030fbe96d1
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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