Sodium Iodide → HCID 54170087, compound

HRID 1170614Notes

Reaction equation

HRID 1170614 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=1)[C:22]([O:24][CH2:25]Cl)=[O:23])=[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-:30].[Na+]>CC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=1)[C:22]([O:24][CH2:25][I:30])=[O:23])=[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 54441965HCID 54441965, compound

Product 1

HCID 54170087HCID 54170087, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of chloromethyl 3-(N-benzyloxycarbonyl-L-valyloxy)-benzoate (2.0 g, 4.76 mmole) in dry acetone (30 ml) was added sodium iodide (3.15 g, 21 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: 2.3 g=94%.

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-b9c4ee1818a64702a49a1e71e0b4f593
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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