Sodium Iodide → HCID 23387351, compound

HRID 1790738Notes

Reaction equation

HRID 1790738 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-00c0d255c13b4f788d44e347479860d8
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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