Sodium Iodide → HCID 23387400, compound

HRID 989973Notes

Reaction equation

HRID 989973 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28]Cl)=[O:26])=[CH:23][CH:22]=1)=[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-:32].[Na+]>CC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][I:32])=[O:26])=[CH:23][CH:22]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 23387568HCID 23387568, compound

Product 1

HCID 23387400HCID 23387400, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of chloromethyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethyl)benzoate (0.5 g, 1.11 mmole). In dry acetone (10 ml) was added sodium iodide (0.75 g, 5.0 mmole) and the mixture was stirred overnight at room temperature. The mixture was evaporated under reduced pressure and extracted with ethyl actate/water. The organic phase was washed with a 5% sodium thiosulfate solution, dried with sodium sulfate and evaporated under reduced pressure. Yield: 0.53 g=88%.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl actate/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-4409d96e4e1548189285fdb871ec1c90
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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