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

HRID 1170571Notes

Reaction equation

HRID 1170571 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-313b1e4d28dc46858ea498349af9eee6
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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