Sodium Iodide → HCID 23387404, compound

HRID 1790793Notes

Reaction equation

HRID 1790793 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH2:29]Cl)=[O:27])=[CH:21][CH:20]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[I-:31].[Na+]>C(#N)C>[C:1]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH2:29][I:31])=[O:27])=[CH:21][CH:20]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 54015566HCID 54015566, compound

Product 1

HCID 23387404HCID 23387404, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Chloromethyl 4-(N-CBZ-L-valyloxy)phenylacetate (0.83 g, 1.9 mmol) and sodium iodide (1.15 g, 7.6 mmol) were heated in acetonitril (45 ml) for 5 h. The mixture was filtrated, the solvent removed, taken up in dichloromethane and filtrated again. Evaporation and purification by chromatography (ether-hexane, 2:3) yielded the title product (0.8 g, 80%).

Workup

  1. filtrationThe mixture was filtrated
  2. customthe solvent removed
  3. filtrationfiltrated again
  4. customEvaporation and purification by chromatography (ether-hexane, 2:3)

Sources & evidence

ORD record
ord-7608148152b84d779098fb4f6a8f574e
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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