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

HRID 1170607Notes

Reaction equation

HRID 1170607 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-b7aad94a60d545c99a6f95031755a761
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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