Sodium Iodide → 3,3-bis-(N-CBz-L-valyloxymethyl)propionic acid iodomethyl ester

HRID 488989Notes

Reaction equation

HRID 488989 reaction equation
Cl[CH2:2][O:3][C:4](=[O:45])[CH2:5][CH:6]([CH2:26][O:27][C:28](=[O:44])[C@H:29]([CH:41]([CH3:43])[CH3:42])[NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:7][O:8][C:9](=[O:25])[C@H:10]([CH:22]([CH3:24])[CH3:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[I-:46].[Na+]>C(#N)C>[I:46][CH2:2][O:3][C:4](=[O:45])[CH2:5][CH:6]([CH2:26][O:27][C:28](=[O:44])[C@H:29]([CH:41]([CH3:43])[CH3:42])[NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:7][O:8][C:9](=[O:25])[C@H:10]([CH:22]([CH3:24])[CH3:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 537927163,3-bis(N-CBz-L-valyloxymethyl)-propionic acid chloromethyl ester

Product 1

HCID 537890083,3-bis-(N-CBz-L-valyloxymethyl)propionic acid iodomethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,3-bis (N-CBz-L-valyloxymethyl)-propionic acid chloromethyl ester (900 mg, 1.38 mmole) was dissolved in acetonitrile (5 ml). Sodium iodide (289 mg, 1.93 mmole) was added to the solution. After reaction at 70° C. for 3 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (5 ml) and refiltered. The solution was dried and gave the titled product. 800 mg.

Workup

  1. customAfter reaction at 70° C. for 3 hr
  2. filtrationthe reaction mixture was filtered
  3. dissolutionthe residue was dissolved in methylene chloride (5 ml)
  4. customThe solution was dried

Sources & evidence

ORD record
ord-fb6c8f5a0b004e6292c2524e24e24ca3
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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