Sodium Iodide → HCID 23387351, compound

HRID 989919Notes

Reaction equation

HRID 989919 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-91d9838693dd4213b9e527938f6334e3
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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