Sodium Iodide → HCID 54008162, compound

HRID 989961Notes

Reaction equation

HRID 989961 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][C:21]([O:23][CH2:24]Cl)=[O:22])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:26].[Na+]>CC(C)=O>[I:26][CH2:24][O:23][C:21](=[O:22])[CH2:20][CH2:19][O:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 53675844HCID 53675844, compound

Product 1

HCID 54008162HCID 54008162, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of chloromethyl 3-(N-benzyloxycarbonyl-L-valyloxy)-propionate (2.05 g, 5.51 mmole) in dry acetone (50 ml) was added sodium iodide (4.12 g, 27.5 mmole) and the mixture was stirred overnight at room temperature. The mixture was evaporated under reduced pressure and extracted with ethyl acetate water. The organic phase was washed with a 5% sodium thiosulfate solution, dried with sodium sulfate and evaporated under reduced pressure. Yield: 2.35 g=92%.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate water
  3. washThe organic phase was washed with a 5% sodium thiosulfate solution
  4. dry with materialdried with sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-438c61cf55fc4ef9997eaa22e380914c
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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