Sodium Iodide → HCID 23387351, compound

HRID 1170572Notes

Reaction equation

HRID 1170572 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]([O:24][CH2:25]Cl)=[O:23])=[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-:27].[Na+]>C(#N)C>[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]([O:24][CH2:25][I:27])=[O:23])=[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 23387518HCID 23387518, compound

Product 1

HCID 23387351HCID 23387351, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(N-CBz-L-valyloxy)ethoxycarbonyloxymethyl chloride (1.16 g, 3 mmole) was dissolved in acetonitrile (10 ml). Sodium iodide (630 g, 4.2 mmole) was added to the solution. After reaction at 65° C. for 2.5 hr, the reaction mixture was cooled down to room temperature and filtered and the residue was dissolved in methylene chloride (5 ml) and refiltered. The solution was dried and gave the titled product. 1.2 g.

Workup

  1. customAfter reaction at 65° C. for 2.5 hr
  2. filtrationfiltered
  3. dissolutionthe residue was dissolved in methylene chloride (5 ml)
  4. customThe solution was dried

Sources & evidence

ORD record
ord-13bc9d9e634440c095082552f566e088
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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