Sodium Iodide → 2,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid iodomethyl ester

HRID 489020Notes

Reaction equation

HRID 489020 reaction equation
Cl[CH2:2][O:3][C:4](=[O:27])[C:5]([CH3:26])([CH3:25])[CH2:6][O:7][C:8](=[O:24])[C@@H:9]([CH:21]([CH3:23])[CH3:22])[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[I-:28].[Na+]>C(#N)C>[I:28][CH2:2][O:3][C:4](=[O:27])[C:5]([CH3:26])([CH3:25])[CH2:6][O:7][C:8](=[O:24])[C@@H:9]([CH:21]([CH3:23])[CH3:22])[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 537919342,2-Dimethyl-3-(N-CBz-D-valyloxy)-propionic acid chloromethyl ester

Product 1

HCID 541922002,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid iodomethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,2-Dimethyl-3-(N-CBz-D-valyloxy)-propionic acid chloromethyl ester (2.4 g, 6 mmole) was dissolved in acetonitrile (30 ml). Sodium iodide (1.26 g, 8.4 mmole) was added to the solution. After reaction at 70° C. for 2 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (20 ml) and refiltered. The solution was dried and gave the titled product. 2.68 g.

Workup

  1. customAfter reaction at 70° C. for 2 hr
  2. filtrationthe reaction mixture was filtered
  3. dissolutionthe residue was dissolved in methylene chloride (20 ml)
  4. customThe solution was dried

Sources & evidence

ORD record
ord-f52f313f8b634979b92494ef28fcfe0a
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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